Hydrochloric Acid → 5'-Propanoylspiro[cyclopropane-1,3'-indoline]-2'-one

HRID 2290507Notes

Reaction equation

HRID 2290507 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:8])[CH2:6][CH3:7].[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]2([CH2:20][CH2:19]2)[C:11]1=[O:21].Cl>CN(C)C=O>[O:8]=[C:5]([C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[NH:10][C:11](=[O:21])[C:12]12[CH2:20][CH2:19]1)[CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12701643Spiro(cyclopropane-1,3'-indolin)-2'-one

Product 1

HCID 137282955'-Propanoylspiro[cyclopropane-1,3'-indoline]-2'-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A slurry was made from 7.5 ml of dimethylformamide and 45.5 g of anhydrous aluminum chloride. The temperature rose to 40° C. and 2.97 ml of propionyl chloride and 5.43 g of spiro[cyclopropane-1,3'-[3H]-indol]-2'(1'H)-one were added. The mixture was stirred for 2 hours at 70° C. and was slowly poured into a mixture of ice and 50 ml of concentrated hydrochloric acid. After cooling overnight, the resulting precipitate was recovered by filtration. Crystallization from ethyl acetate provided 4.9 grams of the desired subtitle intermediate, m.p. 183°-185° C.

Workup

  1. customrose to 40° C.
  2. temperatureAfter cooling overnight
  3. filtrationthe resulting precipitate was recovered by filtration
  4. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-ec65e0e591374a24ad9f28efa9ac0e20
Source dataset
uspto-grants-1986_10
Patent number
US04617302

Reaction notes

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