Aniline → 4-Hydroxy-1-phenylamino-isoquinoline-3-carboxylic acid butyl ester

HRID 523778

Reaction equation

HRID 523778 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10](Br)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CCOC(C)=O>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6115AnilineHCID 860145411-Bromo-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

Product 1

HCID 667127874-Hydroxy-1-phenylamino-isoquinoline-3-carboxylic acid butyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-bromo-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (810 mg, 2.5 mmol, Example D-28 a) and aniline (3 ml) was stirred in a pressure tube in a microwave oven at 150° C. for 20 min. The reaction was repeated on the same scale. Both reaction mixtures were combined, EtOAc (100 ml) was added and the mixture was washed with H2O (5×30 ml, pH=1-2). The organic phase was dried and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using hexanes/EtOAc as the eluent to give 770 mg of 4-hydroxy-1-phenylamino-isoquinoline-3-carboxylic acid butyl ester; MS-(+)-ion: M+1=337.21.

Workup

  1. customBoth reaction mixtures
  2. washthe mixture was washed with H2O (5×30 ml, pH=1-2)
  3. customThe organic phase was dried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-1da82d68f3554d959680304bead38e7b
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Linked notes

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