2-(Acetylamino)-5-aminobenzoic acid → HCID 12270277, compound

HRID 1579894Notes

Reaction equation

HRID 1579894 reaction equation
[CH2:1]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1=O)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.[C:17]([NH:20][C:21]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][C:22]=1[C:23]([OH:25])=[O:24])(=[O:19])[CH3:18]>C(O)(=O)C>[C:17]([NH:20][C:21]1[CH:29]=[CH:28][C:27]([N:30]2[C:11]3[CH2:12][CH2:13][CH2:14][CH2:15][C:10]=3[CH:1]=[C:2]2[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:26][C:22]=1[C:23]([OH:25])=[O:24])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 30169062-(Acetylamino)-5-aminobenzoic acidHCID 105128992-(2-Oxo-2-phenylethyl)cyclohexanone

Product 1

HCID 12270277HCID 12270277, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 11.7 g. (0.054 mole) of 2-phenacylcyclohexanone, 10.5 g. (0.054 mole) of 2-acetamido-5-aminobenzoic acid, and 50 ml. of glacial acetic acid was heated under reflux for 4 hours, cooled, diluted with 15 ml. of methanol and filtered. The collected solid was recrystallized from acetonitrile to provide 9.45 g. (47%) of crystals, m.p. 192° -194°.

Workup

  1. additionA mixture of 11.7 g
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. additiondiluted with 15 ml
  5. filtrationof methanol and filtered
  6. customThe collected solid was recrystallized from acetonitrile
  7. customto provide 9.45 g

Sources & evidence

ORD record
ord-8fab6c3752f04c6ba5cb03cdbadfb81d
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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