Acetic Anhydride → N-(Isoquinolin-3-yl)acetamide

HRID 1913301Notes

Reaction equation

HRID 1913301 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([NH2:18])[N:9]=1.C(N(CC)CC)C>C(Cl)Cl>[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([NH:18][C:5](=[O:7])[CH3:6])[N:9]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 311869Isoquinolin-3-Amine

Product 1

HCID 12366594N-(Isoquinolin-3-yl)acetamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (5.92 mL, 62.6 mmol) was added to a suspension of isoquinolin-3-amine (3.01 g, 20.9 mmol) and triethylamine (3.18 mL, 23.0 mmol) in CH2Cl2 (80 mL) at ambient temperature. The mixture was stirred 3.5 hours, then the volatiles were evaporated in vacuo. The residue was chased with toluene and concentrated in vacuo (3×25 mL) to provide the title compound (3.89 g) as a yellow solid. This material, which was found to also contain small quantities of acetic acid, was used without further purification. 1H NMR (300 MHz, DMSO-d6) δ 10.58 (s, 1H), 9.13 (s, 1H), 8.45 (s, 1H), 8.04 (d, J=7.8 Hz, 1H), 7.88 (d, J=8.2 Hz, 1H), 7.69 (ddd, J=8.2, 6.8, 1.2 Hz, 1H), 7.52 (ddd, J=7.9, 6.9, 1.0 Hz, 1H), 2.13 (s, 3H).

Workup

  1. customthe volatiles were evaporated in vacuo
  2. concentrationconcentrated in vacuo (3×25 mL)

Sources & evidence

ORD record
ord-13996d542cf9459aa0e88551414e0b4f
Source dataset
uspto-grants-2013_12
Patent number
US08609692B2

Reaction notes

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