Methyl 4-(2-chloroethoxy)-5-methoxy-2-nitrobenzoate → Methyl 2-amino-4-(2-chloroethoxy)-5-methoxybenzoate

HRID 1917706Notes

Reaction equation

HRID 1917706 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][Cl:15])=[CH:6][C:5]=1[N+:16]([O-])=O>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:13][CH2:14][Cl:15])=[CH:6][C:5]=1[NH2:16]

Participants

4

Reactant 1

HCID 23032998Methyl 4-(2-chloroethoxy)-5-methoxy-2-nitrobenzoate

Product 1

HCID 23033001Methyl 2-amino-4-(2-chloroethoxy)-5-methoxybenzoateYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(2-chloro-ethoxy)-5-methoxy-2-nitro-benzoic acid methyl ester (2.7 g, 9.32 mmol) in ethyl acetate (30 mL) was added 10% Pd/C (405 mg) and the mixture was stirred under H2 for 12 h. Completion of the reaction was monitored by LCMS. The reaction mixture was filtered using a celite pad and was washed with excess ethyl acetate and evaporated to dryness to afford the pure 2-amino-4-(2-chloro-ethoxy)-5-methoxy-benzoic acid methyl ester (2.40 g, 99%) as a solid. 1H NMR (300 MHz, DMSO-d6) δ 7.15 (s, 1H), 6.40 (s, 2H), 6.35 (s, 1H), 4.18 (t, 2H), 3.95 (t, 2H), 3.70 s, 3H), 3.65 (s, 3H), LC-MS (ESI) m/z 260 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwas washed with excess ethyl acetate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-299fe4b7d1374562acde78e1875e0f1a
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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