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

HRID 909866Notes

Reaction equation

HRID 909866 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)ethanoneYield 97.4%

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 (5.5 g) in acetic acid (55 mL) over 15 min, whilst maintaining the internal temperature below 40° C. with an ice bath. The mixture was allowed to attain ambient temperature and stirred for a further 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 (4.8 g). 1H NMR (300 MHz, DMSO-d6) δ 7.53 (m, 2H), 7.48-7.33 (m, 3H), 7.28 (d, J=9.0 Hz, 1H), 6.72 (d, J=9.0 Hz, 1H), 5.29 (s, 2H), 2.59 (s, 3H).

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-a922e1c2bb5d47f1adccbf721ff18f8e
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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