Ethyl 2-(3-bromo-4-hydroxy-5-nitrophenyl)-4-methylpentanoate → Ethyl 2-(3-amino-5-bromo-4-hydroxyphenyl)-4-methylpentanoate

HRID 385331Notes

Reaction equation

HRID 385331 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[C:6]([N+:9]([O-])=O)[C:7]=1[OH:8]>CO.[OH-].[OH-].[Pd+2]>[NH2:9][C:6]1[CH:5]=[C:4]([CH:12]([CH2:18][CH:19]([CH3:20])[CH3:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:3]=[C:2]([Br:1])[C:7]=1[OH:8]

Participants

4

Reactant 1

HCID 57995502Ethyl 2-(3-bromo-4-hydroxy-5-nitrophenyl)-4-methylpentanoate

Product 1

HCID 57995566Ethyl 2-(3-amino-5-bromo-4-hydroxyphenyl)-4-methylpentanoateYield 72.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution compound ethyl 2-(3-bromo-4-hydroxy-5-nitrophenyl)-4-methylpentanoate (6 g), in dry methanol (100 mL) was added Pd(OH)2 under an atmosphere of nitrogen. The reaction mixture was stirred for 5 h under an atmosphere of hydrogen. The reaction mixture was filtered through Celite™, washed with methanol and concentrated to dryness under reduced pressure. The crude material was purified by column chromatography to yield ethyl 2-(3-amino-5-bromo-4-hydroxyphenyl)-4-methylpentanoate (4 g, 72%). 1HNMR (CDCl3, 200 MHz): 6.80 (s, 1H); 6.62 (s, 1H); 5.35 (bs, 1H); 4.13 (q, 2H); 3.41 (t, 1H); 1.93-1.56 (m, 2H); 1.51 (m, 1H); 1.21 (t, 3H), 0.97 (d, 6H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite™
  2. washwashed with methanol
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-a7b6c39a0b73466abea1d757a084f921
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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