Methyl 5-hydroxy-4-methoxy-2-nitrobenzoate → Methyl 2-amino-5-hydroxy-4-methoxybenzoate

HRID 631205Notes

Reaction equation

HRID 631205 reaction equation
[OH:1][C:2]1[C:3]([O:15][CH3:16])=[CH:4][C:5]([N+:12]([O-])=O)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[H][H]>CCOC(C)=O.[Pd]>[NH2:12][C:5]1[CH:4]=[C:3]([O:15][CH3:16])[C:2]([OH:1])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 53396387Methyl 5-hydroxy-4-methoxy-2-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 23132492Methyl 2-amino-5-hydroxy-4-methoxybenzoateYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

According to the procedure described in Example 6A Step 3, a mixture of methyl 5-hydroxy-4-methoxy-2-nitrobenzoate (3.88 g, 17.1 mmol) and Pd/C in EtOAc (100 mL) was stirred under 1 atmosphere of hydrogen at room temperature overnight, to afford methyl 2-amino-5-hydroxy-4-methoxybenzoate as a solid (3.1 g, 92%). 1H NMR (300 MHz, DMSO-d6) δ 8.31 (s, 1H), 7.08 (s, 1H), 6.31 (s, 1H), 6.24 (s, 1H), 3.74 (s, 3H), 3.72 (s, 3H).

Sources & evidence

ORD record
ord-60f8fd61f31448dc9728271d09f1887a
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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