Acetic Acid → HCID 136242890, compound

HRID 1775198Notes

Reaction equation

HRID 1775198 reaction equation
O=[C:2]1[C:14]2[C:13]3[C:12]([C:15]([O:17]C)=O)=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.C(O)(=O)C.O.[NH2:24][NH2:25]>CO>[CH2:5]1[C:6]2[NH:7][C:8]3[CH:9]=[CH:10][CH:11]=[C:12]4[C:15](=[O:17])[NH:24][N:25]=[C:2]([C:14]=2[C:13]=34)[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 11368514methyl 4-oxo-2,3,4,9-tetrahydro-1H-carbazole-5-carboxylate

Product 1

HCID 136242890HCID 136242890, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound methyl 4-oxo-2,3,4,9-tetrahydro-1H-carbazole-5-carboxylate (73 mg, 0.3 mmol), acetic acid (0.15 mL, 2.6 mmol), and hydrazine hydrate (0.86 mL, 1.5 mmol) in methanol (4 mL) was heated at reflux. After 8 h, the solid was collected by hot filtration and washed with water, EtOAc, and dichloromethane, to give the target compound (42 mg, 62%). 1H NMR (DMSO-d6) δ 11.70 (s, 1H), 9.79 (s, 1H), 7.36-7.38 (m, 2H), 7.05 (t, 1H, J=7.8 Hz), 2.77-2.79 (m, 2H), 2.35-2.37 (m, 2H), and 1.92-1.93 (m, 2H). MS (ESI) m/e [M+1]+ 226.0.

Workup

  1. temperatureat reflux
  2. filtrationthe solid was collected by hot filtration
  3. washwashed with water, EtOAc, and dichloromethane

Sources & evidence

ORD record
ord-acadf7b81ff24030ab91dff309738012
Source dataset
uspto-grants-2016_02
Patent number
US09260440B2

Reaction notes

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