1-(2-Amino-4-methylphenyl)ethan-1-one → HCID 20164596, compound

HRID 1432863Notes

Reaction equation

HRID 1432863 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[N:12]([O-])=O.[Na+]>Cl.O.C([O-])(=O)C.[Na+]>[CH3:8][C:6]1[CH:7]=[C:2]2[C:3]([C:9](=[O:11])[CH:10]=[N:12][NH:1]2)=[CH:4][CH:5]=1

Participants

6

Reactant 2

HCID 139308231-(2-Amino-4-methylphenyl)ethan-1-oneHCID 23668193Sodium Nitrite

Product 1

HCID 20164596HCID 20164596, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 517045Sodium AcetateSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 2-amino-4-methylphenylethanone (5.0 g, 33.6 mmol) in concentrated HCl (100 mL) is treated, in portions, with a solution of sodium nitrite (5.7 g, 82.6 mmol) in water (˜10 mL). The resulting solution is stirred at 60° C. for 2 hr, cooled to ambient temperature and diluted with a saturated solution of sodium acetate (˜200 mL). Solid sodium acetate is added portionwise until the solution tested basic to pH paper. Upon stirring, the title compound precipitated as a white solid which is collected and air dried (2.3 g, 14.3 mmol). MS m/z: [M+H]+=161; 1H NMR (CDCl3, 300 MHz) δ8.1 (d, 1H), 7.85 (s, 1H), 7.45 (s, 1H) 7.3 (d, 1H), 2.55 (s, 3H).

Workup

  1. temperaturecooled to ambient temperature
  2. stirringUpon stirring
  3. customthe title compound precipitated as a white solid which
  4. customis collected
  5. customair dried (2.3 g, 14.3 mmol)

Sources & evidence

ORD record
ord-2c953daf813d43dcba8f4c188fce7e5e
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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