Ammonia → HCID 86733637, compound

HRID 1659115Notes

Reaction equation

HRID 1659115 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([O:12][C:13](=[O:18])[CH2:14][C:15]([CH3:17])=O)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:19][C:20]([F:30])([F:29])[C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=O.[NH3:31].[OH2:32]>C(O)C>[CH2:1]([O:8][CH2:9][CH:10]([O:12][C:13]([C:14]1[CH:23]([C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=2[C:20]([F:30])([F:29])[F:19])[C:14]([C:13]([O:12][CH:10]([CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH3:11])=[O:32])=[C:15]([CH3:17])[NH:31][C:15]=1[CH3:17])=[O:18])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 123067o-(Trifluoromethyl)benzaldehydeHCID 54202166HCID 54202166, compound

Product 1

HCID 86733637HCID 86733637, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of acetoacetic acid (3-benzyloxy-2-propyl) ester (23.8 g), o-trifluoromethylbenzaldehyde (8.7 g.) and concentrated ammonia (10.0 ml. of density 0.88) in ethanol (200 ml) was stirred under reflux for 24 hours and then poured into ice and water. The yellow oil which precipitated was separated and purified by column chromatography to give as a pale yellow oil 1,4-dihydro-2,6-dimethyl-4-(2-trifluoromethylphenyl)pyridine-3,5-dicarboxylic acid bis(3-benzyloxy-2-propyl)ester (24.8 g).

Workup

  1. temperatureunder reflux for 24 hours
  2. customThe yellow oil which precipitated
  3. customwas separated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-b8b2a30e98dd41ddbcc6ec0730a4b1d7
Source dataset
uspto-grants-1976_06
Patent number
US03966946

Reaction notes

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