Diketene → HCID 21320472, compound

HRID 262297Notes

Reaction equation

HRID 262297 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[C:7]1([CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1C=CC=CC=1>[C:4]([N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:14]1)(=[O:5])[CH2:3][C:2]([CH3:1])=[O:6]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 109323533-phenyl-2,3-dihydro-1H-indole

Product 1

HCID 21320472HCID 21320472, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 2.0 g of diketene in 10 ml of dry benzene was added dropwise at 10°-15° C. to a solution of 3.84 g of 3-phenylindoline in 35 ml of dry benzene. The solution was then stirred at room temperature for 90 minutes and the volatile components were removed in vacuo. The residue was recrystallized from ether to give 4.2 g of N-acetoacetyl-3-phenylindoline. A further recrystallization from ethanol gave a purer product having a melting point of 88°-9° C.

Workup

  1. customthe volatile components were removed in vacuo
  2. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-e08ca10a93fa418bbfaf81f53af77c72
Source dataset
uspto-grants-1979_05
Patent number
US04153789

Reaction notes

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