Sodium hydride → 4-Ethoxy-5-ethyl-2-nitroaniline

HRID 2182399Notes

Reaction equation

HRID 2182399 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([CH2:10][CH3:11])=[CH:8][C:7]([NH:12]C(=O)C)=[C:6]([N+:16]([O-:18])=[O:17])[CH:5]=1)[CH3:2].[H-].[Na+].[Cl-].[NH4+]>C(O)C>[CH2:1]([O:3][C:4]1[C:9]([CH2:10][CH3:11])=[CH:8][C:7]([NH2:12])=[C:6]([N+:16]([O-:18])=[O:17])[CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22477728HCID 22477728, compound

Product 1

HCID 224776524-Ethoxy-5-ethyl-2-nitroanilineYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(4-Ethoxy-5-ethyl-2-nitrophenyl)acetamide [0.2 g, Reference Example 32(g)] was dissolved in ethanol (25 mL) and sodium hydride (100 mg; 50% dispersion in mineral oil, 2 mmol) was added. Mixture was stirred overnight at ambient temperature, aq ammonium chloride (3mL) was added and the mixture was evaporated. The residue was chromatographed on silica gel (heptane with gradient of 25-50% ethyl acetate) to give 4-ethoxy-5-ethyl-2-nitrophenylamine (0.1 g) as a red solid. LC-MS (Method E): RT=3.4 minutes, 211 (M+H)+. (h) 5-Chloro-4-methoxy-2-nitrophenylamine

Workup

  1. customthe mixture was evaporated
  2. customThe residue was chromatographed on silica gel (heptane with gradient of 25-50% ethyl acetate)

Sources & evidence

ORD record
ord-cee7aca5aa014160a26474a7c73c958b
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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