Benzene, 2-methoxy-1-methyl-4-nitro- → 3-Methoxy-4-methylaniline

HRID 1618577Notes

Reaction equation

HRID 1618577 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[CH3:12]>[Fe].C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[CH3:12])[NH2:9]

Participants

4

Reactant 1

HCID 83159Benzene, 2-methoxy-1-methyl-4-nitro-

Product 1

HCID 278823-Methoxy-4-methylaniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Prepared according to procedure X using 2-methoxy-1-methyl-4-nitrobenzene (1.66 g, 9.9 mmol), iron powder (1.66 g, 29.8 mmol), and acetic acid (15.0 mL) to give 3-methoxy-4-methylaniline. 1H NMR (500 MHz, DMSO-d6) δ ppm 6.72 (1H, d, J=7.8 Hz), 6.18 (1H, d, J=2.0 Hz), 6.04 (1H, dd, J=7.8, 2.0 Hz), 4.81 (2H, s), 3.67 (3H, s), 1.96 (3H, s).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-e4bf6620bc1b4a70a667382f70bd4fea
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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