2-(3-Methoxy-propyl)-4-nitro-phenoxy-acetic acid ethyl ester → 4-Amino-2-(3-methoxy-propyl)-phenoxy-acetic acid ethyl ester

HRID 1393096Notes

Reaction equation

HRID 1393096 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[CH2:16][CH2:17][CH2:18][O:19][CH3:20])[CH3:2]>CCOC(C)=O.[Pd]>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[CH2:16][CH2:17][CH2:18][O:19][CH3:20])[CH3:2]

Participants

4

Reactant 1

HCID 670724332-(3-Methoxy-propyl)-4-nitro-phenoxy-acetic acid ethyl ester

Product 1

HCID 670720874-Amino-2-(3-methoxy-propyl)-phenoxy-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3.00 g (roughly 65%, 6.56 mmol) of the above prepared [2-(3-methoxy-propyl)-4-nitro-phenoxy]-acetic acid ethyl ester was hydrogenated at RT in 50 ml of EtOAc over 0.60 g of Pd/C (10%) under 1 atm. of H2-pressure. After 3 h at ambient temperature, the reaction mixture was filtered over Celite and carefully rinsed with EtOAc. Evaporation of the solvent, followed by flash chromatography (SiO2, hexane/EtOAc=1/1) produced 1.69 g of the title compound as light brown oil; from the more polar fractions, 0.784 g of 8-(3-methoxy-propyl)-4H-benzo[1,4]oxazin-3-one was isolated (cyclized reduced ortho-amino derivative), MS: 268.3 (MH+)+; side product: 221.1 (M)+.

Workup

  1. filtrationthe reaction mixture was filtered over Celite
  2. washcarefully rinsed with EtOAc
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-c0c183112ea64457ba33a2dc154a4a5a
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

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