Methane → HCID 69135044, compound

HRID 969527Notes

Reaction equation

HRID 969527 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Br:15])[CH:12]=[C:11]([N+:16]([O-])=O)[C:10]=1[NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C.O.NN>CO.[Fe](Cl)(Cl)Cl>[NH2:16][C:11]1[CH:12]=[C:13]([Br:15])[CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]=1[NH:19][C:20](=[O:24])[CH:21]([CH3:22])[CH3:23]

Participants

6

Reactant 3

HCID 297MethaneHCID 24654Hydrazine hydrate (1:1)HCID 69135058HCID 69135058, compound

Product 1

HCID 69135044HCID 69135044, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 25.2 g (64.3 mmol) N-(2benzyloxy-4-bromo-6-nitro-phenyl)-isobutyramide, 6.3 g (38.5 mmol) iron(III) chloride and 15.7 g activated charcoal in 600 ml methanol was heated to 70° C. 31.3 ml (643 mmol). Hydrazine hydrate were added dropwise and the reaction mixture was refluxed for 90 min. After cooling to room temperature the reaction was filtered through celite, the filter cake washed with dichloromethane/methanol and the filtrate concentrated in vacuo. The residue was dried in vacuo at 40° C. to afford 13.0 g (56%) of the title compound as a white solid. m.p. 214°-215° C.

Workup

  1. temperaturethe reaction mixture was refluxed for 90 min
  2. temperatureAfter cooling to room temperature the reaction
  3. filtrationwas filtered through celite
  4. washthe filter cake washed with dichloromethane/methanol
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe residue was dried in vacuo at 40° C.

Sources & evidence

ORD record
ord-c39204ac1fdb42b9b75c2374a437a27e
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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