Synthesis of 4-amino-3-hydroxy-1-naphthalenesulfonic acid

Preparation of 4-amino-3-hydroxy-1-naphthalenesulfonic acid

Preparation of 4-amino-3-hydroxy-1-naphthalenesulfonic acid

Preparation of 4-amino-3-hydroxy-1-naphthalenesulfonic acid

100 g of 2-naphhol are dissolved in 28 g of sodium hydroxide in 1000 ml water and made up to 2000 ml with water. 50 g sodium nitrite dissolved in a little water are carefully added. The mixture is cooled by the addition of 1000 g ice, and 1400 ml 10% sulphuric acid are slowly run in with constant stirring, the temperature being kept below 5° C. The 1-nitroso-2-naphthol separates as a pale yellow precipitate. The moist 1-nitroso-2-naphthol is stirred up with a little water and cooled to 5° with ice. To the paste 260 g sodium bisulphite solution are quickly added. The 1-nitroso-2-naphthol  goes into solution after a few minutes; a small quantity of dilute sodium hydroxide can be cautiously added, if necessary. The solution is filtered to remove resinous matter. The filtered solution is treated at 25° with 100 g conc. sulphuric acid, which has been diluted with 200 g of water. The solution should then give a strongly acid reaction. It is allowed to stand for 1 hour, and it is then warmed to 50° and left overnight—it solidifies to a solid cake. It is filtered off and washed well with water. Yield.—90%. Almost insoluble in cold water, sparingly soluble in hot; sodium salt sparingly soluble in hot water.

Systematic organic chemistry, by W. M. Cumming, 322, 1937.

IUPAC Name

4-amino-3-hydroxynaphthalene-1-sulfonic acid

InChI

InChI=1S/C10H9NO4S/c11-10-7-4-2-1-3-6(7)9(5-8(10)12)16(13,14)15/h1-5,12H,11H2,(H,13,14,15)

InChI Key

RXCMFQDTWCCLBL-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C2C(=C1)C(=CC(=C2N)O)S(=O)(=O)O

MeSH Synonyms

1-amino-2-naphthol-4-sulfonic acid, ANSK compound

Depositor-Supplied Synonyms

116-63-2, 4-Amino-3-hydroxy-1-naphthalenesulfonic acid, 1-Amino-2-naphthol-4-sulfonic acid, 4-Amino-3-hydroxynaphthalene-1-sulfonic acid, 1-Amino-4-sulfo-2-naphthol, 1,2,4-Acid, 4-Amino-3-hydroxynaphthalenesulfonic acid, 1-NAPHTHALENESULFONIC ACID, 4-AMINO-3-HYDROXY-, CHEBI:19024, 4-Amino-3-hydroxynaphthalene-1-sulphonic acid, 1,2,4-Aminonaphtholsulfonic acid, 2-Hydroxy-4-sulfo-1-naphthylamine, EINECS 204-147-3, NSC 25061, AI3-03701, 4-Amino-3-Hydroxy-1-Naphdialene Sulfonic Acid, 4-amino-3-hydroxy-naphthalene-1-sulfonic acid, C10H9NO4S, 4-AMINO-3-HYDROXY-1-NAPHTHALENE SULFONIC ACID, 1-Amino-2-Naphthol-4-Sulfonic Acid Hydrate, AC1L1QQE, ACMC-1ARS7, AC1Q6WV7, UNII-W46SK3P33G, Ambap116-63-2, ARONIS23873, SCHEMBL153735, 109754_ALDRICH, AC1Q516F, W46SK3P33G, Jsp001171, CHEMBL2312198, 08751_FLUKA, CTK0H6535, RXCMFQDTWCCLBL-UHFFFAOYSA-, NSC4986, MolPort-001-779-885, RXCMFQDTWCCLBL-UHFFFAOYSA-N, BB_SC-0049, 398969_SIAL, NSC-4986, NSC25061, ZINC1680647, ANW-16980, AR-1G0662, BBL007892, NSC-25061, SBB008870, STK387126, 4-NH2-3-OH-naphthalenesulfonic acid, AKOS001483109, MCULE-1459423123, RTR-030797, AC-11577, AJ-29621, AK117775, AN-22761, KB-64857, LS-94890, OR006116, TR-030797, 4-amino-3-hydroxy-1-napthalenesulfonic acid, A0367, FT-0607319, ST24043221, ST45053712, 1-Naphthalenesulfonic acid,4-amino-3-hydroxy-, 1-Naphthalenesulfonicacid, 4-amino-3-hydroxy-, Z-0800, S09-0118, W-108579, 3B3-012846, InChI=1/C10H9NO4S/c11-10-7-4-2-1-3-6(7)9(5-8(10)12)16(13,14)15/h1-5,12H,11H2,(H,13,14,15)

Removed Synonyms

ANSA, Ambap129, CID8316, A1922, 118694-03-4, 567-13-5

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