Hydrochloric Acid → HCID 178479639, compound

HRID 902045Notes

Reaction equation

HRID 902045 reaction equation
[ClH:1].[C:2]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])(=[O:4])[CH3:3].[N:12]([O-])=O.[Na+]>O>[ClH:1].[N:7]1[C:6]2[C:5](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:2]([OH:4])=[CH:3][N:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 110862'-AminoacetophenoneHCID 23668193Sodium Nitrite

Product 1

HCID 178479639HCID 178479639, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

560 ml of concentrated hydrochloric acid are introduced into a reactor. 111.6 g of 2-acetylaniline are added at ambient temperature. 62.8 g of sodium nitrite, in solution in 170 ml of water, are added to this orange-colored solution at −5° C. over 1 hour. The temperature is kept below 0° C. throughout the introduction. The reaction medium is heated at 65° C. for 3 hours. The mixture is subsequently cooled over 20 minutes and the product is then filtered off and washed with ether. The compound is dried over P2O5 at 45° C. overnight. 118.6 grams (77%) of the expected product are obtained.

Workup

  1. customis kept below 0° C. throughout the introduction
  2. temperatureThe mixture is subsequently cooled over 20 minutes
  3. filtrationthe product is then filtered off
  4. washwashed with ether
  5. dry with materialThe compound is dried over P2O5 at 45° C. overnight

Sources & evidence

ORD record
ord-1d13be1a2a6442cb8602a2f72aa94dbd
Source dataset
uspto-grants-2008_04
Patent number
US07365071B2

Reaction notes

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