Ethyl pyruvate → HCID 66909220, compound

HRID 1969442Notes

Reaction equation

HRID 1969442 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O.[NH2:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1.[C:23]([O:28]CC)(=O)[C:24]([CH3:26])=O>C(O)(=O)C>[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:5]=[C:6]([CH:7]2[N:14]([C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=3)[C:23](=[O:28])[C:24]([NH:14][C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=3)=[CH:26]2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 12041Ethyl pyruvateHCID 133964-AminobenzonitrileHCID 6051393-(Trifluoromethoxy)benzaldehyde

Product 1

HCID 66909220HCID 66909220, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Add 3-(trifluoromethoxy)benzaldehyde (10.0 g, 52.6 mmol) to a solution of 4-aminobenzonitrile (18.6 g, 157.8 mmol) in glacial acetic acid (53 mL). Stir at ambient temperature for 20 min. and a precipitate forms. Add ethyl pyruvate (5.8 mL, 52.6 mmol). Stir at ambient temperature for 18 hours. Filter the precipitate and wash with glacial acetic acid and then with 1:1 hexanes-diethyl ether to afford the titled compound (12.8 g, 53%). LC-MS ESI m/z: 461 (M+H)+, 459 (M−1)−, Tr=3.05 min., method 2.

Workup

  1. stirringStir at ambient temperature for 18 hours
  2. filtrationFilter the precipitate
  3. washwash with glacial acetic acid

Sources & evidence

ORD record
ord-c6b99636ff504b79bce065659686f07f
Source dataset
uspto-grants-2013_04
Patent number
US08426448B2

Reaction notes

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