Acetyl chloride → 1-acetyl-2,3-dihydro-5-methoxy-1H-indole-2-carboxamide

HRID 887923Notes

Reaction equation

HRID 887923 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]([C:23]([NH2:25])=[O:24])[CH2:17]2>C(Cl)Cl>[C:8]([N:19]1[C:20]2[C:16](=[CH:15][C:14]([O:13][CH3:12])=[CH:22][CH:21]=2)[CH2:17][CH:18]1[C:23]([NH2:25])=[O:24])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 219140882,3-dihydro-5-methoxy-1H-indole-2-carboxamide

Product 1

HCID 219141281-acetyl-2,3-dihydro-5-methoxy-1H-indole-2-carboxamideYield 53.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.0106 mole) then acetyl chloride (0.0106 mole) were added to a solution of intermediate (21) (0.0032 mole) in DCM (40 ml) cooled in an ice bath under argon. The mixture was allowed to slowly warm to room temperature and stir overnight. The mixture was cooled in an ice bath and ice cold water (30 ml) was added. After stirring for 10 minutes, the mixture was filtered, and the solid was allowed to dry overnight. The residue was suspended in 50 ml water. The suspension was allowed to stir for 30 minutes, filtered, and dried overnight, yielding 0.40 g of 1-acetyl-2,3-dihydro-5-methoxy-1H-indole-2-carboxamide (intermediate 22, mp. 196-197° C.).

Workup

  1. temperaturecooled in an ice bath under argon
  2. temperatureThe mixture was cooled in an ice bath
  3. stirringAfter stirring for 10 minutes
  4. filtrationthe mixture was filtered
  5. customto dry overnight
  6. stirringto stir for 30 minutes
  7. filtrationfiltered
  8. customdried overnight

Sources & evidence

ORD record
ord-70956710f9e14680970063701ba274c7
Source dataset
uspto-grants-2012_08
Patent number
US08247432B2

Reaction notes

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