Ammonia → HCID 44537318, compound

HRID 1659114Notes

Reaction equation

HRID 1659114 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12](=[O:17])[CH2:13][C:14]([CH3:16])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]([F:29])([F:28])[C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O.[NH3:30].[OH2:31]>C(O)C>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]([C:13]1[CH:22]([C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[C:19]([F:29])([F:28])[F:18])[C:13]([C:12]([O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:31])=[C:14]([CH3:16])[NH:30][C:14]=1[CH3:16])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 123067o-(Trifluoromethyl)benzaldehydeHCID 140251412-(Benzyloxy)ethyl 3-oxobutanoate

Product 1

HCID 44537318HCID 44537318, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of acetoacetic acid 2-benzyloxyethyl ester (30 g), o-trifluoromethyl benzaldehyde (11.2 g) and concentrated ammonia (8.0 ml of density 0.88) in ethanol (100 ml) was stirred under reflux for 24 hours and then poured into ice and water. The yellow oil which precipitated was separated, and solidified on addition of ethanol. Recrystallisation from ethanol gave 1,4-dihydro-2,6-dimethyl-4-(2-trifluoromethylphenyl)pyridine 3,5-dicarboxylic acid bis-(2-benzyloxyethyl)ester (10.4 g), as white crystals m.p. 141°-142°C.

Workup

  1. temperatureunder reflux for 24 hours
  2. customThe yellow oil which precipitated
  3. customwas separated
  4. additionsolidified on addition of ethanol
  5. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-99e47310413942cc87ae7205b7e4af34
Source dataset
uspto-grants-1976_06
Patent number
US03966946

Reaction notes

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