Acetic Acid → HCID 68047234, compound

HRID 658565Notes

Reaction equation

HRID 658565 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:13])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([NH:8][NH2:9])=[O:7].[CH:14]1([CH:20]=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(O)(=O)C>C(O)C>[CH:14]1([CH:20]=[N:9][NH:8][C:6](=[O:7])[C:5]2[CH:10]=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[C:4]=2[CH3:13])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 16275CyclohexanecarboxaldehydeHCID 450912733-Methoxy-2-methylbenzohydrazide

Product 1

HCID 68047234HCID 68047234, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.0 g (55.5 mmol) of 3-methoxy-2-methyl-benzoic acid hydrazide was dissolved in 200 mL of absolute ethyl alcohol. Cyclohexanecarbaldehyde (6.85 g, 61.0 mmol) and glacial acetic acid (3 mL) were added, and the reaction mixture was stirred for 18 h while monitoring by TLC. The precipitate was collected by filtration and washed with hexane. Product 3-methoxy-2-methyl-benzoic acid cyclohexylmethylene-hydrazide was obtained as a white solid (9.36 g, yield 61%): Rf=0.20 (3:1 EtOAc:n-Hexane); 1H NMR (400 MHz, CDCl3) δ 11.17 (s, 1H), 7.91 (s, 1H), 7.50 (d, J=4.8 Hz, 1H), 7.25 (t, J=6.4 Hz, 1H), 6.99 (t, J=5.6 Hz, 1H), 3.89 (s, 3H), 2.28 (s, 3H), 1.92-1.62 (m, 5H), 1.38-1.14 (m, 6H); HRMS (ESI) m/z calcd for C16H23N2O2 [M+H]+ 275.1760, found 275.1752, calcd for C16H22N2NaO2 [M+Na]+ 297.1579, found 297.1568.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with hexane

Sources & evidence

ORD record
ord-9f216661615f49dc9af06bba1fbf02fc
Source dataset
uspto-grants-2011_12
Patent number
US08076517B2

Reaction notes

Loading…