Trichloroacetyl chloride → 2,2,2-trichloro-N-isoquinolin-5-ylacetamide

HRID 887174Notes

Reaction equation

HRID 887174 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[Cl:12][C:13]([Cl:18])([Cl:17])[C:14](Cl)=[O:15]>ClCCl.CCN(CC)CC>[Cl:12][C:13]([Cl:18])([Cl:17])[C:14]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2)=[O:15]

Participants

5

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 707665-Aminoisoquinoline

Product 1

HCID 88932512,2,2-trichloro-N-isoquinolin-5-ylacetamideYield 65.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 5-aminoisoquinoline (1.0 g, 6.9 mmol) in dichloromethane (40 mL) and Et3N (1 mL) at 5° C. was treated with trichloroacetyl chloride (1.38 g, 7.6 mmol) dropwise. The reaction mixture was stirred at ambient temperature for 14 hours, concentrated, diluted with ethyl acetate and washed with 1N HCl. The aqueous layer was treated with aqueous NaHCO3 and extracted with ethyl acetate. The organic layer the was washed with water and concentrated. The solid residue was suspended in ethyl acetate (5 mL) and filtered to obtain 1.3 g (65%) of the title compound as a tan solid. 1H NMR (300 MHz, d6-DMSO) δ 11.20 (broad s, 1H), 9.41, (s, 1H), 8.60 (d, 1H), 8.18 (m, 1H), 7.77 (m, 2H), 7.66 (d, 1H); MS (DCI/NH3) m/z 289 (M+H)+.

Workup

  1. concentrationconcentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with 1N HCl
  4. additionThe aqueous layer was treated with aqueous NaHCO3
  5. extractionextracted with ethyl acetate
  6. washThe organic layer the was washed with water
  7. concentrationconcentrated
  8. filtrationfiltered

Sources & evidence

ORD record
ord-a6b1b1df59a04ff08cb65567d59327af
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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