Water → N-(7-(5-fluoro-2-methylphenyl)isoquinolin-3-yl)acetamide

HRID 468786Notes

Reaction equation

HRID 468786 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:19])=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH2:18])[N:14]=[CH:15]3)=[CH:10][CH:9]=2)[CH:7]=1.[C:20](Cl)(=[O:22])[CH3:21].O>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:19])=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH:18][C:20](=[O:22])[CH3:21])[N:14]=[CH:15]3)=[CH:10][CH:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 574102447-(5-Fluoro-2-methylphenyl)isoquinolin-3-amine

Product 1

HCID 67974795N-(7-(5-fluoro-2-methylphenyl)isoquinolin-3-yl)acetamideYield 15.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 7-(5-fluoro-2-methylphenyl)isoquinolin-3-amine (150 mg, 0.595 mmol) in pyridine (2 mL) was added acetyl chloride (56 mg, 0.714 mmol) dropwise at a temperature below 0° C. After the resulting mixture was stirred at room temperature for 2 h, water (2 mL) was added and it was concentrated under reduced pressure. The solid was washed with methanol and water to give the desired product (26.7 mg, 15.2%). LCMS (ESI): RT (min)=1.150, M+H+=294.8, method=A; 1H NMR (400 MHz, DMSO-d6) δ 10.62, (s, 1H), 9.14 (s, 1H), 8.47 (s, 1H), 8.00 (s, 1H), 7.93 (d, J=8.0 Hz, 1H), 7.68 (d, J=6.8 Hz, 1H), 7.35 (s, 1H), 7.15 (d, J=8.8 Hz, 2H), 2.22 (s, 3H), 2.12 (s, 3H).

Workup

  1. concentrationit was concentrated under reduced pressure
  2. washThe solid was washed with methanol and water

Sources & evidence

ORD record
ord-f4a01cf834b8492fa1559633d5540cc6
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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