Phthalic Anhydride → Benzoic acid, 2-[(1-butyl-2-methyl-1H-indol-3-yl)carbonyl]-

HRID 2051733Notes

Reaction equation

HRID 2051733 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH2:12]([N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[C:17]1[CH3:25])[CH2:13][CH2:14][CH3:15].[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1>[CH2:12]([N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([C:4]([C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[C:1]([OH:6])=[O:11])=[O:5])=[C:17]1[CH3:25])[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 30848831H-Indole, 1-butyl-2-methyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 105559Benzoic acid, 2-[(1-butyl-2-methyl-1H-indol-3-yl)carbonyl]-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred mixture containing 7.4 g. of phthalic anhydride and 16.0 g. of 1-butyl-2-methylindole at 0°-5° C. was added portionwise 13.3 g. of aluminum chloride. The mixture was diluted with 50 ml. of benzene and stirred overnight at room temperature. The reaction mixture was poured into 200 ml. of 5% hydrochloric acid and the product extracted with benzene. The benzene extracts were shaken with dilute aqueous potassium hydroxide. The aqueous alkaline layer was separated, cooled with ice and brought to pH 4 with acetic acid. The precipitated product was collected and dried to give 2-(1-butyl-2-methyl-3-indolylcarbonyl)benzoic acid, m.p. 88°-92° C.

Workup

  1. additionTo a stirred mixture containing 7.4 g
  2. additionThe mixture was diluted with 50 ml
  3. additionThe reaction mixture was poured into 200 ml
  4. extractionof 5% hydrochloric acid and the product extracted with benzene
  5. customThe aqueous alkaline layer was separated
  6. temperaturecooled with ice
  7. customThe precipitated product was collected
  8. customdried

Sources & evidence

ORD record
ord-f2a9450cd3744c658ba102d80e665897
Source dataset
uspto-grants-1980_01
Patent number
US04182714

Reaction notes

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