Ethanol → HCID 19878630, compound

HRID 1885501Notes

Reaction equation

HRID 1885501 reaction equation
[CH2:1]([O:8][C:9]([N:11]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=1[OH:22])[CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([OH:25])[CH3:24].C(OC(=O)C)(=O)C>[Fe].C(O)(=O)C>[C:23]([NH:19][C:16]1[CH:17]=[CH:18][C:13]([N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH3:12])=[C:14]([OH:22])[CH:15]=1)(=[O:25])[CH3:24]

Participants

6

Reactant 3

HCID 702EthanolHCID 7918Acetic AnhydrideHCID 19878626HCID 19878626, compound

Product 1

HCID 19878630HCID 19878630, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

3.3×10-2 mole (10 g) of 2-(N-benzyloxycarbonyl -N-methylamino)-5-nitrophenol is added to 40 g of iron powder in 60 ml of 96° strength ethanol mixed with 20 ml of acetic acid brought to 80° C., the temperature being maintained at 80° C. When the addition is complete, heating is maintained for 30 minutes. The inorganic salts present in the reaction medium are removed by filtration while hot. The filtrate is diluted with 800 ml of ice-cold water. 3.7×10-2 mole (3.5 ml) of acetic anhydride is then added. The expected product crystallizes after 3 hours. After filtration and drying, the product obtained is recrystallized from a water/ethanol mixture. It then melts at 174° C.

Workup

  1. custombrought to 80° C.
  2. additionWhen the addition
  3. temperatureheating
  4. temperatureis maintained for 30 minutes
  5. customThe inorganic salts present in the reaction medium are removed by filtration while hot
  6. additionThe filtrate is diluted with 800 ml of ice-cold water
  7. customThe expected product crystallizes after 3 hours
  8. filtrationAfter filtration
  9. customdrying
  10. customthe product obtained
  11. customis recrystallized from a water/ethanol mixture

Sources & evidence

ORD record
ord-11d1e49f7eeb41b0a3223b16f6439ca5
Source dataset
uspto-grants-1992_09
Patent number
US05145483

Reaction notes

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