4-Oxocyclohexanecarboxylic acid → HCID 67360248, compound

HRID 1664488Notes

Reaction equation

HRID 1664488 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.Cl.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19]N>C(O)(=O)C>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:14]=1[NH:19][C:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][C:3]2=1

Participants

4

Reactant 2

HCID 1927304-Oxocyclohexanecarboxylic acidHCID 4432872-Chlorophenylhydrazine hydrochloride

Product 1

HCID 67360248HCID 67360248, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-oxo-cyclohexanecarboxylic acid (3.1 g, 21.7 mmol) and 2-chlorophenylhydrazine hydrochloride (4.0 g, 21.7 mmol) in glacial acetic acid (740 ml) is stirred at reflux for 3 h. The solvent is evaporated and water is added to the residue. The resulting precipitate is filtered off and dried under high vacuum to give the subtitle compound as a brownish solid (4.5 g) in 83% yield. tR (LC-5) 0.88 min; ESI-MS (positive ion): m/z 250.14 [M+H]+ (calcd 249.70 for C13H12NO2Cl). 1H-NMR (DMSO-d6): 1.75 (m, 1H); 2.14 (m, 1H); 2.62 (m, 5H); 6.90 (t, J=7.9 Hz, 1H); 7.02 (d, J=7.3 Hz, 1H); 7.30 (d, J=7.6 Hz, 1H); 7.92 (br s, 1H); 10.9 (br s, 1H).

Workup

  1. temperatureat reflux for 3 h
  2. customThe solvent is evaporated
  3. additionwater is added to the residue
  4. filtrationThe resulting precipitate is filtered off
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-ddd2575236734e4b8104469547f2fbbf
Source dataset
uspto-grants-2011_10
Patent number
US08039474B2

Reaction notes

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