Ammonia → 1-Amino-7-isoquinolinol

HRID 636968

Reaction equation

HRID 636968 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][N:13]=[C:14]2[NH2:17])=[CH:9][CH:8]=1.N>ClCCl>[NH2:17][C:14]1[C:15]2[C:10](=[CH:9][CH:8]=[C:7]([OH:6])[CH:16]=2)[CH:11]=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 226656441-Isoquinolinamine, 7-methoxy-

Product 1

HCID 226313131-Amino-7-isoquinolinolYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide (35 mL) in 50 mL of dichloromethane was added dropwise to a stirred solution of 7-methoxy-isoquinolin-1-ylamine (21.6 g) in 70 mL of dichloromethane at 10° C. After stirring for 4 d at ambient temperature the reaction mixture was poured on ice and the pH adjusted to pH 9 by adding concentrated aqueous ammonia. The precipitated material was collected by filtration and dried in vacuo to give 19.3 g (97%) of the title compound as a light brownish solid. M.p. 260° C. (decomp.); EI-MS: 160 (M+).

Workup

  1. additionwas poured on ice
  2. filtrationThe precipitated material was collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-e004a9509c724c2eb0d040d7ef34f49e
Source dataset
uspto-grants-2001_02
Patent number
US06194409B1

Linked notes

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