Methyl 4-methoxy-5-(2-methoxyethoxy)-2-nitrobenzoate → Methyl 2-amino-4-methoxy-5-(2-methoxyethoxy)benzoate

HRID 631231Notes

Reaction equation

HRID 631231 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([N+:18]([O-])=O)[CH:4]=1.[H][H]>CCOC(C)=O.[Pd]>[NH2:18][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 58394383Methyl 4-methoxy-5-(2-methoxyethoxy)-2-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 58394329Methyl 2-amino-4-methoxy-5-(2-methoxyethoxy)benzoateYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

According to the procedure described in Example 6A Step 3, a mixture of methyl 4-methoxy-5-(2-methoxyethoxy)-2-nitrobenzoate (3.67 g, 12.9 mmol) and Pd/C (10%, 0.4 g) in EtOAc (60 mL) was stirred under 1 atmosphere of hydrogen at room temperature overnight, to afford methyl 2-amino-4-methoxy-5-(2-methoxyethoxyl)benzoate as a solid (3.05 g, 93%). 1H NMR (300 MHz, DMSO-d6) δ 7.15 (s, 1H), 6.46 (s, 2H), 6.36 (s, 1H), 3.91 (m, 2H), 3.75 (s, 3H), 3.74 (s, 3H), 3.59 (m. 2H), 3.32 (s, 3H).

Sources & evidence

ORD record
ord-05efcd38dd944892bc3a51353dec6951
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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