Chloroacetyl chloride → HCID 57950333, compound

HRID 930658Notes

Reaction equation

HRID 930658 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][N:13]([C:16]2[CH:24]=[C:23]3[C:19]([C:20]4[CH2:29][CH2:28][N:27](CCO)[CH2:26][C:21]=4[N:22]3[CH3:25])=[CH:18][CH:17]=2)[C:12](=[O:33])[CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])(O)=O.[Na+].[Cl:39][CH2:40][C:41](Cl)=[O:42]>C(Cl)Cl>[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][N:13]([C:16]2[CH:24]=[C:23]3[C:19]([C:20]4[CH2:29][CH2:28][N:27]([C:41](=[O:42])[CH2:40][Cl:39])[CH2:26][C:21]=4[N:22]3[CH3:25])=[CH:18][CH:17]=2)[C:12](=[O:33])[CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 68658158HCID 68658158, compound

Product 1

HCID 57950333HCID 57950333, compoundYield 112.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(Benzyloxy)-1-(2-(2-hydroxyethyl)-9-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-7-yl)pyridin-2(1H)-one hydrochloride (100 mg, 0.23 mmol) was stirred in a mixture of CH2Cl2 (2 mL) and saturated NaHCO3 solution (2 mL) and chloroacetyl chloride (32 mg, 0.28 mmol) was added. After 1.5 h, the organic layer was removed and concentrated to provide the title compound (120 mg, 100%) as a yellow oil: ESI MS m/z 462 [M+H]+.

Workup

  1. additionwas added
  2. customthe organic layer was removed
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-69afbaf7f5634f75b69be863ccb4ef01
Source dataset
uspto-grants-2016_03
Patent number
US09296743B2

Reaction notes

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