Ethanol → HCID 68125287, compound

HRID 441269Notes

Reaction equation

HRID 441269 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[NH:7][C:8](=[O:14])/[CH:9]=[C:10](\[O:12][CH3:13])/[CH3:11])([O-])=O.C(O)C>[Fe].O>[NH2:1][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[NH:7][C:8](=[O:14])/[CH:9]=[C:10](\[O:12][CH3:13])/[CH3:11]

Participants

5

Reactant 2

HCID 702EthanolHCID 68125441HCID 68125441, compound

Product 1

HCID 68125287HCID 68125287, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
27 °C

Procedure

48 g of powdered iron were added over 15 minutes at 20° C. to a mixture of 18.9 g of m-nitro-3-methoxy-crotonanilide, 64 ml of 95% ethanol, 16 ml of water and 0.8 ml of 22° Be hydrochloric acid and the mixture was stirred for 11/2 hours at 27° C. The interior temperature was raised to 60° C. and the temperature was slowly lowered to 25° C. The mixture was filtered and the filtrate was evaporated to dryness under reduced pressure to obtain 13.6 g of m-amino-3-methoxy-crotonanilide. The product melted at 132° C. and after crystallization from ethanol still melted at 132° C.

Workup

  1. temperatureThe interior temperature was raised to 60° C.
  2. customwas slowly lowered to 25° C
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4cddbd06bbfc40cc859a0fd79318b250
Source dataset
uspto-grants-1977_08
Patent number
US04039316

Reaction notes

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