Diketene → HCID 21320472, compound

HRID 1679280Notes

Reaction equation

HRID 1679280 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-phenylindolin 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-32122a9736764b40b33a27e2ea68b4b6
Source dataset
uspto-grants-1978_03
Patent number
US04080330

Reaction notes

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