Anthranilic Acid → HCID 21569606, compound

HRID 1579862Notes

Reaction equation

HRID 1579862 reaction equation
[CH2:1]([CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=O)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.[C:21]([OH:30])(=[O:29])[C:22]1[C:23](=[CH:25][CH:26]=[CH:27][CH:28]=1)[NH2:24]>C(O)(=O)C>[C:21]([C:22]1[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=1[N:24]1[C:11]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[CH2:18][CH2:19][C:10]=2[CH:1]=[C:2]1[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([OH:30])=[O:29]

Participants

4

Reactant 2

HCID 227Anthranilic AcidHCID 122703462-phenacyl-1-tetralone

Product 1

HCID 21569606HCID 21569606, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 20.0 g. (0.076 mole) of 2-phenacyl-1-tetralone, 9.86 g. (0.072 mole) of anthranilic acid, and 70 ml. of glacial acetic acid was heated under reflux for 501/2 hours and concentrated to an oil, which crystallized from isopropyl alcohol to provide 10.7 g. (41%) of solid, m.p. 170°-185°. Recrystallization from ethanol-water, isopropyl alcohol, and cyclohexane-methanol gave 4.0 g. of yellow crystals, m.p. 223.5°-224.5°.

Workup

  1. additionA mixture of 20.0 g
  2. temperatureunder reflux for 501/2 hours
  3. concentrationconcentrated to an oil, which
  4. customcrystallized from isopropyl alcohol
  5. customto provide 10.7 g
  6. customRecrystallization from ethanol-water, isopropyl alcohol, and cyclohexane-methanol
  7. customgave 4.0 g

Sources & evidence

ORD record
ord-ae90019c763041aeace72cf359bffcb6
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

Loading…