Anthranilic Acid → 2-(isopropylamino)benzoic acid

HRID 652303Notes

Reaction equation

HRID 652303 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[C:11](O)(=O)[C:12]1C(=CC=C[CH:20]=1)C(O)=O.[BH4-].[Na+]>CC(C)=O>[CH:12]([NH:4][C:3]1[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([OH:10])=[O:9])([CH3:20])[CH3:11]

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 1017Phthalic AcidHCID 4311764Sodium borohydride

Product 1

HCID 122277122-(isopropylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To stirred mixture of 2.7 g. of anthranilic acid and 5.4 g. of phthalic acid in 23 ml. of acetone is added 0.7 g. of powdered sodium borohydride over a period of 30 minutes at 20° C.-30° C. The resulting slurry is then stirred at 35°-40° C. for 4 hours, diluted with 25 ml. of chloroform and filtered. The filtrate is concentrated in vacuo and the residue dissolved in 20 ml. of chloroform and treated with 30 ml. of hexane, filtered and the filtrate concentrated in vacuo to obtain a crude solid product which is recrystallized 5 times from cyclohexane to obtain (second crop of fifth recrystallization) N-isopropylanthranilic acid, m.p. 109°-109.5° C.

Workup

  1. additionmixture of 2.7 g
  2. stirringThe resulting slurry is then stirred at 35°-40° C. for 4 hours
  3. additiondiluted with 25 ml
  4. filtrationof chloroform and filtered
  5. concentrationThe filtrate is concentrated in vacuo
  6. dissolutionthe residue dissolved in 20 ml
  7. additionof chloroform and treated with 30 ml
  8. filtrationof hexane, filtered
  9. concentrationthe filtrate concentrated in vacuo
  10. customto obtain a crude solid product which
  11. customis recrystallized 5 times from cyclohexane

Sources & evidence

ORD record
ord-da4aecf33b69426fad5521a1237919b9
Source dataset
uspto-grants-1987_06
Patent number
US04670600

Reaction notes

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