Methane → HCID 69134397, compound

HRID 969536Notes

Reaction equation

HRID 969536 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:27])[CH:21](C(=O)CC)[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:27])[CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 297MethaneHCID 24654Hydrazine hydrate (1:1)HCID 86607444HCID 86607444, compound

Product 1

HCID 69134397HCID 69134397, compoundYield 112.2%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 22 g (48.5 mmol) N-(2-benzyloxy-4-bromo-6-nitro-phenyl)-propionyl-propionamide, 4.9 g (30 mmol) iron(III) chloride and 7.2 g activated charcoal in 180 ml methanol was heated to 70° C. 23.8 ml (490 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, the filtrate reduced in volume and poured into water. The precipitate was filtered and washed with diethyl ether to afford 19 g (89%) of the title compound as a white solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 90 min
  2. temperatureAfter cooling to room temperature
  3. filtrationthe reaction was filtered through celite
  4. washthe filter cake washed with dichloromethane
  5. additionpoured into water
  6. filtrationThe precipitate was filtered
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-3a2c09f31499477f89c2c1e958899ec8
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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