Ethanol → N-(7-methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-yl)-isobutyramide

HRID 545506Notes

Reaction equation

HRID 545506 reaction equation
C(Cl)(=O)C.C(O)C.Cl.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([NH:17]N)[CH:14]=[CH:15][CH:16]=1.O=[C:20]1[CH2:25][CH2:24][CH:23]([NH:26][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])[CH2:22][CH2:21]1>C(OCC)(=O)C>[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:14]([C:21]3[CH2:22][CH:23]([NH:26][C:27](=[O:31])[CH:28]([CH3:29])[CH3:30])[CH2:24][CH2:25][C:20]=3[NH:17]2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6367Acetyl chlorideHCID 27239403-Methoxyphenylhydrazine hydrochlorideHCID 215339942-Methyl-N-(4-oxocyclohexyl)propanamide

Product 1

HCID 59161215N-(7-methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-yl)-isobutyramideYield 31.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Follow the procedures essentially as described in Preparation 6, above, using acetyl chloride (26 mL, 360 mmol) and absolute ethanol (90 mL) with 3-methoxyphenylhydrazine hydrochloride (5.24 g, 30 mmol) and N-(4-oxo-cyclohexyl)-isobutyramide (5.50 g, 30 mmol). When complete, dilute the reaction with ethyl acetate (200 mL) and wash with 0.5N NaOH and sodium bicarbonate solution. Filter the solids in the organic phase, triturate in dichloromethane and filter to give 2.67 g (31%) gray solid. MS (ES): m/z 287 (M+1), 285 (M−1); 1H NMR(DMSO-d6): δ 10.52 (s, 1H), 7.83 (d, 1H, J=7.5 Hz), 7.21 (d, 1H, J=8.4 Hz), 6.78 (s, 1H), 6.60 (d, 1H, J=8.4 Hz), 4.00 (m, 1H), 3.75 (s, 3H), 2.87 (dd, 1H, J=14.8, 5.1 Hz), 2.76 (m, 2H), 2.48-2.36 (m, 2H), 2.48-2.36 (m, 2H), 1.76 (m, 1H), 1.03 (d, 6H, J=6.6 Hz).

Workup

  1. customas described in Preparation 6
  2. additionWhen complete, dilute
  3. washwash with 0.5N NaOH and sodium bicarbonate solution
  4. filtrationFilter the solids in the organic phase
  5. customtriturate in dichloromethane
  6. filtrationfilter

Sources & evidence

ORD record
ord-8f72a4b9037442e9b4f7ba28d4052d7b
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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