Hydrochloric Acid → 2-(9-Ethyl-9H-carbazole-3-carbonyl)benzoic acid

HRID 1413895Notes

Reaction equation

HRID 1413895 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[C:16]1(=[O:26])[O:21][C:19](=[O:20])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClC1C=CC=CC=1>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:16]([C:17]3[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=3[C:19]([OH:21])=[O:20])=[O:26])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6811Phthalic AnhydrideHCID 6836N-ethyl carbazoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 204713592-(9-Ethyl-9H-carbazole-3-carbonyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To a mixture of 8.14 g (0.05 mole) of N-ethylcarbazole and 3.7 g (0.025 mole) of phthalic anhydride in 112 g of chlorobenzene, 6.65 g (0.05 mole) of aluminum chloride was added in small increments at ambient temperature after which the mixture was warmed in the range of 50°-70° C. for two hours. The reaction mixture was poured onto ice and rendered acidic by the addition of 10 percent hyrochloric acid. The chlorobenzene layer was separated and steam-distilled to remove the chlorobenzene. The residue was extracted with 10 percent aqueous sodium hydroxide, filtered to remove the insolubles and then acidified with dilute hydrochloric acid. The solid which separated was collected by filtration, washed with water and dried to obtain 2-[(9-ethyl-3-carbazolyl)carbonyl]benzoic acid (Formula VII: R0 =R1 =R2 =Rhu 3=H; R8 =CH2CH3) melting over the range 120°-130° C.

Workup

  1. additionwas added in small increments at ambient temperature after which the mixture
  2. temperaturewas warmed in the range of 50°-70° C. for two hours
  3. additionThe reaction mixture was poured onto ice
  4. customThe chlorobenzene layer was separated
  5. distillationsteam-distilled
  6. customto remove the chlorobenzene
  7. extractionThe residue was extracted with 10 percent aqueous sodium hydroxide
  8. filtrationfiltered
  9. customto remove the insolubles
  10. customThe solid which separated
  11. filtrationwas collected by filtration
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-a3e6171aea3c46bdbeb734256907b96e
Source dataset
uspto-grants-1981_02
Patent number
US04251446

Reaction notes

Loading…