Levulinic Acid → 5H-1,3-Dioxolo(4,5-f)indole-7-acetic acid, 5-(p-chlorobenzoyl)-6-methyl-

HRID 1282988Notes

Reaction equation

HRID 1282988 reaction equation
Cl.[Cl:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([N:9]([C:11]2[CH:16]=[CH:15][C:14]3[O:17][CH2:18][O:19][C:13]=3[CH:12]=2)N)=[O:8])=[CH:5][CH:4]=1.[C:22]([OH:29])(=[O:28])[CH2:23][CH2:24][C:25]([CH3:27])=O>O>[Cl:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([N:9]2[C:11]3[C:16](=[CH:15][C:14]4[O:17][CH2:18][O:19][C:13]=4[CH:12]=3)[C:24]([CH2:23][C:22]([OH:29])=[O:28])=[C:25]2[CH3:27])=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 11579Levulinic AcidHCID 21395963HCID 21395963, compound

Product 1

HCID 377885H-1,3-Dioxolo(4,5-f)indole-7-acetic acid, 5-(p-chlorobenzoyl)-6-methyl-Yield 55.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.9 g of N1 -(p-chlorobenzoyl)-3,4-methylenedioxyphenylhydrazine hydrochloride and 20 g of levulinic acid was heated for 1 hour at 55° - 60°C and for 3 hours at 80° - 90°C. The reaction mixture was cooled to a room temperature, and poured into 200 ml of water. The precipitates were collected by filtration and washed with water. The crystals obtained by twice recrystallizing from acetone-water (5 : 1) gave 1.19 g of 1-(p-chlorobenzoyl)-2-methyl-5,6-methylenedioxy-3-indolylacetic acid having a melting point of 217° - 218°C.

Workup

  1. temperaturewas heated for 1 hour at 55° - 60°C and for 3 hours at 80° - 90°C
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with water
  4. customThe crystals obtained
  5. customby twice recrystallizing from acetone-water (5 : 1)

Sources & evidence

ORD record
ord-c518379d655a47a0b5beab3f86901e75
Source dataset
uspto-grants-1976_08
Patent number
US03974145

Reaction notes

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