Cyclohexanone → HCID 66606744, compound

HRID 1811141Notes

Reaction equation

HRID 1811141 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[C:10]([NH:17]N)[CH:9]=1.[C:19]1(=O)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[C:10]2[C:9]=1[C:19]1[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=1[NH:17]2

Participants

4

Reactant 2

HCID 7967CyclohexanoneHCID 66605946HCID 66605946, compound

Product 1

HCID 66606744HCID 66606744, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Step 4 A solution of 2′-fluoro-3-hydrazinylbiphenyl-4-carboxylic acid (0.306 g, 1.24 mmol) and cyclohexanone (0.183 g, 1.86 mmol) in acetic acid (6.2 mL) was heated at reflux under nitrogen for 2 h. The mixture was cooled to rt and concentrated. The residue was partitioned between EtOAc and 1 M hydrochloric acid. The organic layer was washed with brine, dried and concentrated. The residue was triturated with EtOAc and DCM to give 5-(2-fluorophenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid (0.132 g) as a white solid. The filtrate was purified by column chromatography (eluting with a gradient from hexane to 50:50 EtOAc-hexane) to give additional product (0.029 g, 41% total). 1H NMR (400 MHz, DMSO-d6) δ 12.95 (br s, 1 H), 10.79 (s, 1 H), 7.68 (d, J=7.15, 1 H), 7.42-7.51 (m, 1 H), 7.24-7.34 (m, 3 H), 6.87 (d, J=7.15, 1 H), 2.67-2.82 (m, 2 H), 1.89-2.10 (m, 2 H), 1.65-1.81 (m, 2 H), 1.44-1.63 (m, 2 H). Mass spectrum m/z 310.1 (M+H)+.

Workup

  1. temperatureat reflux under nitrogen for 2 h
  2. concentrationconcentrated
  3. customThe residue was partitioned between EtOAc and 1 M hydrochloric acid
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was triturated with EtOAc and DCM

Sources & evidence

ORD record
ord-033d137e1c6647deb39fa29871717dea
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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