Chloroacetyl chloride → 1-(2-Chloroacetyl)-3,3-dimethylindoline-6-carbonitrile

HRID 1475409Notes

Reaction equation

HRID 1475409 reaction equation
[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:12])=[CH:8][CH:9]=2)[NH:4][CH2:3]1.C(N(CC)CC)C.[Cl:21][CH2:22][C:23](Cl)=[O:24]>C(Cl)Cl.O>[Cl:21][CH2:22][C:23]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:11]#[N:12])[CH:6]=2)[C:2]([CH3:13])([CH3:1])[CH2:3]1)=[O:24]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 107023412,3-dihydro-3,3-dimethyl-1H-indole-6-carbonitrile

Product 1

HCID 867240061-(2-Chloroacetyl)-3,3-dimethylindoline-6-carbonitrileYield 78.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,3-dimethylindoline-6-carbonitrile (0.35 g, 2.0 mmol) and triethylamine (0.56 mL, 4.0 mmol) in DCM (10 mL) at 0° C. was added chloroacetyl chloride (0.16 mL, 2.0 mmol) dropwise. The reaction was warmed to room temperature and stirred overnight. The reaction mixture was then diluted with water. The organic phase was then separated, dried over magnesium sulfate and concentrated to give the title compound (0.39 g). 1H NMR (CDCl3): 8.47 (s, 1H), 7.40 (d, 1H), 7.24 (d, 1H), 4.14 (s, 2H), 3.94 (s, 2H), 1.42 (s, 6H).

Workup

  1. customThe organic phase was then separated
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d5f0e16947f44766a9f737d75b2fa2f5
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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