Ethanol → 4-[(2-Methoxy-6-methylpyridin-4-yl)oxy]-N2-methylbenzene-1,2-diamine

HRID 1843721Notes

Reaction equation

HRID 1843721 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:11]=[CH:12][C:13]([N+:18]([O-])=O)=[C:14]([CH:17]=2)[NH:15][CH3:16])[CH:6]=[C:5]([CH3:21])[N:4]=1.[Cl-].[NH4+].C(O)C>[Fe].O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:17]=[C:14]([NH:15][CH3:16])[C:13]([NH2:18])=[CH:12][CH:11]=2)[CH:6]=[C:5]([CH3:21])[N:4]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 667057765-[(2-Methoxy-6-methylpyridin-4-yl)oxy]-N-methyl-2-nitroaniline

Product 1

HCID 667058364-[(2-Methoxy-6-methylpyridin-4-yl)oxy]-N2-methylbenzene-1,2-diamineYield 100.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

The reaction and post-treatment were carried out according to Example (1b) using 5-[(2-methoxy-6-methylpyridin-4-yl)oxy]-N-methyl-2-nitroaniline produced in Example (17b) (4.87 g, 16.8 mmol), iron powder (4.70 g, 84.2 mmol), ammonium chloride (0.45 g, 8.42 mmol), ethanol (80 mL) and water (40 mL) to obtain the title compound (4.37 g, 99%) as a brown oil.

Workup

  1. customThe reaction

Sources & evidence

ORD record
ord-c203749a251d46dfb84dcb90df95f61a
Source dataset
uspto-grants-2015_02
Patent number
US08946264B2

Reaction notes

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