1-(benzyloxy)-4,5-dimethoxy-2-nitrobenzene → HCID 20341030, compound

HRID 1394992Notes

Reaction equation

HRID 1394992 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[CH:11][C:10]=1[N+:19]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.C(O)(=O)C.O.[Fe]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[CH:11][C:10]=1[NH2:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 1

HCID 2840471-(benzyloxy)-4,5-dimethoxy-2-nitrobenzene

Product 1

HCID 20341030HCID 20341030, compound

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a hot suspension (60° C.) of 260 g 2-benzyloxy-4,5-dimethoxy-nitrobenzene in 900 ml of ethanol, 1350 ml of glacial acetic acid and 900 ml of water, 282.6 g of iron powder was added portion-wise over 30 min. Thereafter the mixture was refluxed for 1/4 h. The reaction mixture was poured into 10 l of water and the oily product was extracted with dichloromethane. After drying the solvent was evaporated. Yield: 116 g (50%). Melting point: 74° C.

Workup

  1. temperatureThereafter the mixture was refluxed for 1/4 h
  2. extractionthe oily product was extracted with dichloromethane
  3. customAfter drying the solvent
  4. customwas evaporated

Sources & evidence

ORD record
ord-e372bbc145524fc0893a2c3bd677e0ac
Source dataset
uspto-grants-1980_05
Patent number
US04201584

Reaction notes

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