Synthesis of 4-aminoisoquinoline

Preparation of 4-aminoisoquinoline

Preparation of 4-aminoisoquinoline

Preparation of 4-aminoisoquinoline

A mixture of 50 g. of 4-bromoisoquinoline, 160 ml. of concentrated ammonium hydroxide solution, and 3 g. of copper sulfate 5-hydrate is heated in a shaking autoclave at 165-170° for 16 hours. The reaction mixture is made alkaline with dilute sodium hydroxide solution and extracted with five 100-ml. portions of benzene. After being dried over anhydrous potassium carbonate and treated with charcoal, the benzene solution is concentrated to a volume of 70 ml. Cooling precipitates 24 g. (70%) of 4-aminoisoquinoline, m.p. 107-107.5°. Two recrystallizations from benzene raise the melting point to 108.5°.

J. Am. Chem. Soc., 64, 783 (1942).

IUPAC Name

isoquinolin-4-amine

InChI

InChI=1S/C9H8N2/c10-9-6-11-5-7-3-1-2-4-8(7)9/h1-6H,10H2

InChI Key

ISIUXVGHQFJYHM-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C2C(=C1)C=NC=C2N

Depositor-Supplied Synonyms

4-Aminoisoquinoline, isoquinolin-4-amine, 23687-25-4, 4-Isoquinolylamine, 4-Isoquinolinamine, 4-Amino-isoquinoline, isoquinolin-4-ylamine, Isoquinoline, 4-amino-, ISIUXVGHQFJYHM-UHFFFAOYSA-N, AE-842/31875006, NSC170840, isoquinolin-4-yl-amine, PubChem12825, AC1Q4YCQ, AC1L3JK0, 4-AMINO ISOQUINOLINE, KSC204Q8H, SCHEMBL1325881, CTK1A4883, MolPort-000-140-380, ZINC332648, ACT10454, EINECS 245-823-8, AB1274, ANW-51242, AR-1G3001, CA-987, RW3246, SBB051995, WTI-10866, ZINC00332648, AKOS006345437, AN-1258, MCULE-9842095851, NSC-170840, PS-4545, QC-2269, RP01408, RTC-061987, TRA0040422, VQ10179, AJ-19550, AK-24246, BC675984, BR-24246, CJ-02851, HE021692, HE248454, KB-36527, L613, ZB010655, AB0014797, DB-006655, KB-254555, KB-254558, ST2413164, TC-061987, WT-131007, 4CH-002305, AM20070002, FT-0080451, FT-0600553, FT-0662070, C-1064, I14-0519, W-206846, 3B3-017857, InChI=1/C9H8N2/c10-9-6-11-5-7-3-1-2-4-8(7)9/h1-6H,10H

Removed Synonyms

CID90237, A2595, 24269-80-5

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