Thionyl Chloride → HCID 178474844, compound

HRID 722936Notes

Reaction equation

HRID 722936 reaction equation
[C:1]([NH:4][CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([OH:14])=O)[CH2:8][CH2:7]1)(=[O:3])[CH3:2].S(Cl)([Cl:17])=O>>[C:1]([NH:4][CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([Cl:17])=[O:14])[CH2:8][CH2:7]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 178474847HCID 178474847, compound

Product 1

HCID 178474844HCID 178474844, compound

Procedure

trans-4-[(Acetylamino)methyl]cyclohexanecarboxylic acid (12.1 g) was added by portions to thionyl chloride (25 ml) under ice-cooling. After stirred at room temperature for 30 minutes, thionyl chloride was evaporated under reduced pressure to give crude crystals of trans-4-[(acetylamino)methyl]cyclohexanecarbonyl chloride. Then, aluminum chloride (24.0 g) was added by portions to a solution of the crude crystals and 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (12.1 g) in dichloromethane (30 ml) under ice-cooling. After stirring at room temperature for 12 hours, the reaction mixture was poured into ice (300 g), extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound as colorless crystals (12.9 g) having a melting point of 178 to 180° C.

Workup

  1. temperaturecooling
  2. customthionyl chloride was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9e94a8b2629748bc98ab7bc4f2a6094d
Source dataset
uspto-grants-2006_11
Patent number
US07138533B2

Reaction notes

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