Hydrochloric Acid → 6-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-one

HRID 28671Notes

Reaction equation

HRID 28671 reaction equation
ClC1C=CC(N[N:9]=[C:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2=[O:16])=CC=1.[ClH:17]>C(O)(=O)C>[Cl:17][C:10]1[CH:11]=[C:12]2[C:13](=[CH:14][CH:15]=1)[NH:9][C:10]1[C:11](=[O:16])[CH2:12][CH2:13][CH2:14][C:15]2=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57289360Cyclohexane-1,2-dione (4-chlorophenyl)hydrazone

Product 1

HCID 6129776-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-oneYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of cyclohexane-1,2-dione (4-chlorophenyl)hydrazone (2.3 g, 9.7 mmol) in hydrochloric acid (2 mL) and acetic acid (8 mL) was heated at 120° C. for 20 minutes. The mixture was cooled slightly and treated with ice water. The resulting precipitate was collected by filtration to give 6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (1.9 g, 88% yield) as brown solid. 1H-NMR (DMSO-d6): δ 11.78 (s, 1H), 7.75 (m, 1H), 7.38 (d, 1H), 7.28 (dd, 1H), 2.92 (t, 2H), 2.55 (t, 2H), 2.13 (q, 2H); MS m/z 220 (M+1).

Workup

  1. temperatureThe mixture was cooled slightly
  2. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-c919f64e9bed4b3489f565778dac985b
Source dataset
uspto-grants-2008_09
Patent number
US07419997B2

Reaction notes

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