Ethanol → HCID 21478799, compound

HRID 1604629Notes

Reaction equation

HRID 1604629 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:22]([O-])=O)=[C:13]([CH2:15][C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].C(O)C>[Fe].O>[NH2:22][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][C:13]=1[CH2:15][C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 19603840HCID 19603840, compound

Product 1

HCID 21478799HCID 21478799, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of isopropyl 5-benzyloxy-2-nitrophenylacetate (4.2 g), ammonium chloride (0.42 g) and iron powder (4.2 g) in a mixed solvent of ethanol (20 ml) and water (10 ml) was stirred at 80° C. for 1.2 hours. After cooling, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was partitioned between water and ethyl acetate and the ethyl acetate layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give isopropyl 2-amino-5-benzyloxyphenylacetate (3.9 g).

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was partitioned between water and ethyl acetate
  5. washthe ethyl acetate layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-482e9a04746b4307a72df8d58c9fc0b7
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

Loading…