Methyl 5-methoxy-4-(2-methoxyethoxy)-2-nitrobenzoate → HCID 66876535, compound

HRID 871239Notes

Reaction equation

HRID 871239 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:5][C:6]([N+:13]([O-])=O)=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9].[H][H]>CCOC(C)=O.[Pd]>[NH2:13][C:6]1[CH:5]=[C:4]([O:16][CH2:17][CH2:18][O:19][CH3:20])[C:3]([O:2][CH3:1])=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 2

HCID 66876504Methyl 5-methoxy-4-(2-methoxyethoxy)-2-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 66876535HCID 66876535, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

According to the procedure described in Example 6A Step 3, a mixture of methyl 5-methoxy-4-(2-methoxyethoxy)-2-nitrobenzoate (3.19 g, 11.2 mmol) and Pd/C (10%, 0.3 g) in EtOAc (150 mL) was stirred under 1 atmosphere of hydrogen at room temperature for 6 hours, to afford methyl 2-amino-5-methoxy-4-(2-methoxyethoxy)benzoate as a solid (2.699 g, 95%). 1H NMR (300 MHz, CDCl3) δ 7.30 (s, 1H), 6.17 (s, 1H), 5.55 (br, 2H), 4.14 (t, 2H), 3.85 (s, 3H), 3.80 (s, 3H), 3.79 (t, 2H), 3.44 (s, 3H); LC-MS (ESI) m/z 256 (M+H)+.

Sources & evidence

ORD record
ord-180ce8e3002040d2b5f4583ba22f386e
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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