Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoate → Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate

HRID 1917655Notes

Reaction equation

HRID 1917655 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:16]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:8]([N+:22]([O-])=O)[CH:7]=1.[H][H]>CCOC(C)=O.[Pd]>[NH2:22][C:8]1[CH:7]=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[C:16]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:15][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 2

HCID 11186961Ethyl 4,5-bis(2-methoxyethoxy)-2-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 11347513Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoateYield 92%

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-bis(2-methoxyethoxy)-2-nitrobenzoate (8.53 g, 24.8 mmol) and Pd/C (10%, 0.85 g) in EtOAc (150 mL) was stirred under 1 atmosphere of hydrogen at room temperature overnight, to afford ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate as an oil (7.15 g, 92%). 1H NMR (300 MHz, CDCl3) δ 7.44 (s, 1H), 6.15 (s, 1H), 5.60 (br, 2H), 4.30 (q, 2H), 4.13 (t. 2H), 4.08 (t, 2H), 3.78 (t, 2H), 3.73 (t. 2H), 3.45 (s, 6H), 1.36 (t, 3H); LC-MS (ESI) m/z 314 (M+H)+.

Sources & evidence

ORD record
ord-fe6c5b1e3b114c9a9386bb7238609a74
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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