Acetic Acid → HCID 68047234, compound

HRID 335674Notes

Reaction equation

HRID 335674 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-c50c34dbb766404e83962f7bb4c11b8b
Source dataset
uspto-grants-2014_11
Patent number
US08884060B2

Reaction notes

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