5-(2,6-Dimethyl-4-nitrophenoxy)-2-(2-methoxyethoxymethoxy)benzoic acid 2-methoxyethoxymethyl ester → 5-(4-Amino-2,6-dimethylphenoxy)-2-(2-methoxyethoxymethoxy)benzoic acid 2-methoxyethoxymethyl ester
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8](=[O:34])[C:9]1[CH:14]=[C:13]([O:15][C:16]2[C:21]([CH3:22])=[CH:20][C:19]([N+:23]([O-])=O)=[CH:18][C:17]=2[CH3:26])[CH:12]=[CH:11][C:10]=1[O:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33]>[Pd].CCOC(C)=O>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8](=[O:34])[C:9]1[CH:14]=[C:13]([O:15][C:16]2[C:17]([CH3:26])=[CH:18][C:19]([NH2:23])=[CH:20][C:21]=2[CH3:22])[CH:12]=[CH:11][C:10]=1[O:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of the title A compound, 5-(2,6-dimethyl-4-nitrophenoxy)-2-(2-methoxy-ethoxymethoxy)benzoic acid 2-methoxyethoxymethyl ester (3.2 g, 6.68 mmol) and palladium on activated carbon (10 wt. %; 320 mg) in 50 mL of EtOAc is stirred under hydrogen atmosphere (H2, 1 atm) for 3 h. The catalyst is removed by vacuum filtration through celite, washed with EtOAc, and the combined filtrate and washings are concentrated and dried under vacuum to give 5-(4-amino-2,6-dimethylphenoxy)-2-(2-methoxyethoxymethoxy)benzoic acid 2-methoxy-ethoxymethyl ester: NMR (CDCl3) 2.07 (s, 6H), 3.37 (s, 3H), 3.40 (s, 3H), 3.52-3.62 (m, 4H), 3.83-3.92 (m, 4H), 5.26 (s, 2H), 5.52 (s, 2H), 6.60 (s, 2H), 6.80 (dd, 1H, J=8.3, 3), 7.13 (d, 1H, J=8.3), 7.24 (d, 1H, J=3).
Workup
- customThe catalyst is removed by vacuum filtration through celite
- washwashed with EtOAc
- concentrationthe combined filtrate and washings are concentrated
- customdried under vacuum
Sources & evidence
- ORD record
- ord-22347467c9ac4b0fa0a74d0e0fd838e8
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06689896B2
Reaction notes
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