Ethyl 4,5-diethoxy-2-nitrobenzoate → Ethyl 2-amino-4,5-diethoxybenzoate

HRID 871262Notes

Reaction equation

HRID 871262 reaction equation
[CH2:1]([O:3][C:4]1[C:14]([O:15][CH2:16][CH3:17])=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([N+:18]([O-])=O)[CH:5]=1)[CH3:2].[H][H]>CCOC(C)=O.[Pd]>[NH2:18][C:6]1[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[C:14]([O:15][CH2:16][CH3:17])=[CH:13][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 2

HCID 11022393Ethyl 4,5-diethoxy-2-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 11807180Ethyl 2-amino-4,5-diethoxybenzoateYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

According to the procedure described in Example 6A Step 3, a mixture of ethyl 4,5-diethoxy-2-nitrobenzoate (7.17 g, 25.3 mmol) and Pd/C (10%, 0.7 g) in EtOAc (150 mL) was stirred under 1 atmosphere of hydrogen at room temperature overnight, to afford ethyl 2-amino-4,5-diethoxybenzoate as a solid (6.401 g, 99%) 1H NMR (300 MHz, CDCl3) δ 7.36 (s, 1H), 6.14 (s, 1H), 5.60 (br, 2H), 4.30 (q, 2H), 4.05 (m, 4H), 1.44 (t, 3H), 1.38 (m, 6H); LC-MS (ESI) m/z 254 (M+H)+.

Sources & evidence

ORD record
ord-2db66caaa6f34488b230acad519e48b2
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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