4-Bromophenylhydrazine hydrochloride → HCID 46098126, compound

HRID 545499Notes

Reaction equation

HRID 545499 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.O=[C:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:23])[CH:20]([CH3:22])[CH3:21])[CH2:14][CH2:13]1>Cl>[Br:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][C:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:23])[CH:20]([CH3:21])[CH3:22])[CH2:14][C:13]2=1

Participants

4

Reactant 2

HCID 121574-Bromophenylhydrazine hydrochlorideHCID 215339942-Methyl-N-(4-oxocyclohexyl)propanamide

Product 1

HCID 46098126HCID 46098126, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Combine p-bromophenylhydrazine hydrochloride (10.0 g, 44.7 mmol) and N-(4-oxo-cyclohexyl)isobutyramide (8.20g, 44.7 mmol) in saturated ethanolic HCl (180 mL) and heat at reflux under nitrogen for 18 h. Concentrate in vacuo to remove about ½ of the EtOH, then dilute with water (300 mL). Collect the resulting solid, slurry in EtOAc and recollect to give 11.5 g (77%) of a beige solid. MS (ES): 335 (M+1), 337 (M+H+2). 1H NMR(DMSO-d6): δ 10.93 (s, 1H, NH), 7.80 (d, 1H, J=7.9 Hz), 7.48 (s, 1H), 7.19 (d, 1H, J=8.8 Hz), 7.07 (d, 1H, J=8.4 Hz), 4.00 (m, 1H), 2.86 (dd, 1H, J=15.2, 5.1 Hz), 2.77 (m, 2H), 2.46-2.32 (m, 2H), 1.93 (m, 1H), 1.75 (m, 1H), 0.99 (d, 6H, J=6.6 Hz).

Workup

  1. temperatureat reflux under nitrogen for 18 h
  2. concentrationConcentrate in vacuo
  3. customto remove about ½ of the EtOH
  4. additiondilute with water (300 mL)
  5. customCollect the resulting solid

Sources & evidence

ORD record
ord-ccc98e5f1e3542a0957e368c9b048259
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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