3-(Trifluoromethyl)benzaldehyde → HCID 140350464, compound

HRID 845586Notes

Reaction equation

HRID 845586 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:26])=[C:5]([C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][OH:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[F:27][C:28]([F:38])([F:37])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]=O)[CH:30]=1>>[CH3:1][C:2]1[NH:3][C:4]([CH3:26])=[C:5]([C:20]([O:22][CH:23]([CH3:24])[CH3:25])=[O:21])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N:18](=[CH:35][C:31]3[CH:32]=[CH:33][CH:34]=[C:29]([C:28]([F:27])([F:37])[F:38])[CH:30]=3)=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

3

Reactant 2

HCID 679903-(Trifluoromethyl)benzaldehydeHCID 14183059HCID 14183059, compound

Product 1

HCID 140350464HCID 140350464, compound

Procedure

The reaction of hydroxylamine 82 (0.71 g, 2 mmol) with α,α,α-trifluoro-m-tolualdehyde (60) (0.348 g, 2 mmol) afforded, after workup, a light yellow solid. The crude product was recrystallized from ether/petroleum ether to obtain 0.80 g (1.55 mmol. 78%) of 85 as a white crystalline solid: mp 127°-129° C.; IR (CH2Cl2) 3440, 2980, 1698, 1624, 1558, 1475, 1332, 1300, 1215, 1100, 1018, 810 cm-1 ; 1H NMR (CDCl3) δ 1.14 (d, J=6.2 Hz, 3H), 1.26 (d, J=6.2 Hz, 3H), 2.29 (s, 6H), 3.65 (s, 3H), 4.97 (septet, J=6.2 Hz, 1H), 5.08 (s, 1H), 6.47 (br s, 1H), 7.28-8.76 (m, 9H); 13C NMR (CDCl3) δ 19.48, 21.99, 22.22, 39.98, 51.15, 67.31, 102.99, 103.70, 119.43, 121.55, 125.52, 125.55, 127.22, 128.56, 129.28, 130.43, 131.46, 131.92, 133.40, 144.79, 145.33, 148.92, 149.91, 167.01, 168.03. Anal. Calcd for C27H27N2O5F3 : C, 62.79; H, 5.23. Found: C, 62.68; H, 5.02.

Workup

  1. customafforded
  2. customThe crude product was recrystallized from ether/petroleum ether

Sources & evidence

ORD record
ord-c86e237e92fb4a16a8f9dd6bda272654
Source dataset
uspto-grants-1988_07
Patent number
US04758669

Reaction notes

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