1-[4-(Benzyloxy)-2-hydroxy-3-nitrophenyl]ethan-1-one → 1-(3-Amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone

HRID 1689215Notes

Reaction equation

HRID 1689215 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([OH:18])[C:10]=1[N+:19]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[NH2:19][C:10]1[C:11]([OH:18])=[C:12]([C:15](=[O:17])[CH3:16])[CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 579889911-[4-(Benzyloxy)-2-hydroxy-3-nitrophenyl]ethan-1-one

Product 1

HCID 579892521-(3-Amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc dust (5.5 g) was added portionwise to a suspension of 1-(4-(benzyloxy)-2-hydroxy-3-nitrophenyl)ethanone (example 11, step b) (5.5 g) in acetic acid (55 mL) over 15 minutes, whilst maintaining the internal temperature below 40° C. with an ice bath. The mixture was allowed to attain ambient temperature and stirred for 2 h. The mixture was filtered through Celite (Caution: Gets hot—do not allow to dry), washed with acetic acid, and the filtrate poured onto ice/water (500 mL). The resulting precipitate was filtered off, washed with water, and dried under vacuum at 40° C. to afford the subtitled compound as a light brown solid. Yield 4.8 g.

Workup

  1. temperaturewhilst maintaining the internal temperature below 40° C. with an ice bath
  2. customto attain ambient temperature
  3. filtrationThe mixture was filtered through Celite (Caution
  4. customto dry),
  5. washwashed with acetic acid
  6. additionthe filtrate poured onto ice/water (500 mL)
  7. filtrationThe resulting precipitate was filtered off
  8. washwashed with water
  9. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-da37aae32a44434697388ff6f4081380
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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