Hydrochloric Acid → 1-(4-Amino-2-chloro-6-methylphenyl)ethanone

HRID 1465581Notes

Reaction equation

HRID 1465581 reaction equation
[C:1]([C:4]1[C:9]([CH3:10])=[CH:8][C:7]([NH:11]C(=O)C)=[CH:6][C:5]=1F)(=[O:3])[CH3:2].[ClH:16].[OH-].[Na+]>C(O)C>[NH2:11][C:7]1[CH:8]=[C:9]([CH3:10])[C:4]([C:1](=[O:3])[CH3:2])=[C:5]([Cl:16])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86690882N-(4-Acetyl-3-fluoro-5-methylphenyl)acetamide

Product 1

HCID 584424271-(4-Amino-2-chloro-6-methylphenyl)ethanoneYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An ethanol solution (51 mL) containing N-(4-acetyl-3-fluoro-5-methylphenyl)acetamide (30-2, 5.80 g, 27.7 mmol) and concentrated hydrochloric acid (20.0 mL) was heated at reflux for 15 h. The solution was added with 10% aqueous NaOH and the resultant solids were collected to give 1-(4-amino-2-chloro-6-methylphenyl)ethanone (30-3, 4.00 g, 23.9 mmol) as light yellow solids in 86% yield: 1H NMR (500 MHz, DMSO-d6) δ 6.22 (m, 2 H), 2.37 (m, 3 H), 2.22 (s, 3 H). ESI-MS: m/z 167.8 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 15 h
  3. customthe resultant solids were collected

Sources & evidence

ORD record
ord-3dc2eef2e39c4c23bbf64ec8a00c6239
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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