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

HRID 1465670Notes

Reaction equation

HRID 1465670 reaction equation
[C:1]([C:4]1[C:9]([CH3:10])=[CH:8][C:7]([NH:11]C(=O)C)=[CH:6][C:5]=1[Cl:15])(=[O:3])[CH3:2].Cl.[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:15])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58442558N-(4-acetyl-3-chloro-5-methylphenyl)acetamide

Product 1

HCID 584424271-(4-Amino-2-chloro-6-methylphenyl)ethanoneYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An ethanol solution (4.0 mL) containing N-(4-acetyl-3-chloro-5-methylphenyl)acetamide (0.53 g, 2.3 mmol) and concentrated hydrochloric acid (1.6 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 (0.37 g) as light yellow solids in 88% yield: 1H NMR (500 MHz, CDCl3) δ 6.46 (d, J=1.77 Hz, 1 H), 6.34 (s, 1 H), 3.85 (bs, 2 H), 2.49 (s, 3 H), 2.14 (s, 3 H): ESI-MS: m/z 183.4 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-f401bd4fec7e498497ce0396fce2ba5c
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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