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

HRID 1413635Notes

Reaction equation

HRID 1413635 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-].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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 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. extractionthe product extracted with benzene
  4. customThe aqueous alkaline layer was separated
  5. temperaturecooled with ice
  6. customThe precipitated product was collected
  7. customdried

Sources & evidence

ORD record
ord-52414744bce14502b2c8c4f9f0acfb4e
Source dataset
uspto-grants-1981_02
Patent number
US04251092

Reaction notes

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