Hydrochloric Acid → HCID 21563738, compound

HRID 1580720Notes

Reaction equation

HRID 1580720 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][CH2:16][C:17]#[N:18])[C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=1.[C:19]1(=[O:29])[O:24][C:22](=[O:23])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1C=CC=CC=1>[C:22]([C:21]1[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=1[C:19]([C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH2:15][CH2:16][C:17]#[N:18])[C:12]3[C:4]([C:5]=2[CH:6]=1)=[CH:3][C:2]([CH3:1])=[CH:14][CH:13]=3)=[O:29])([OH:24])=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6811Phthalic AnhydrideHCID 6451240Aluminum(III) ChlorideHCID 54454176HCID 54454176, compound

Product 1

HCID 21563738HCID 21563738, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of the compound prepared in step (a) (0.03 mole), phthalic anhydride (0.03 mole) and 50 ml. of benzene were stirred in an ice bath. Aluminum chloride (0.065 mole) was slowly added to the mixture, and after addition, the mixture was stirred for 30 minutes at 0°C. and then warmed to 50°C. and stirred for 3 hours. After cooling, 3N hydrochloric acid was added to decompose the aluminum complex. The yellow solid that formed was filtered and stirred in warm dilute ammonium hydroxide. The hydroxide solution was filtered, and the filtrate was neutralized with dilute hydrochloric acid. The solid obtained upon neutralization was recrystallized from xylene to give 3-(o-carboxybenzoyl)-6-methyl-9-cyanoethylcarbazole as white crystals, melting point 190°C.

Workup

  1. additionafter addition
  2. temperaturewarmed to 50°C.
  3. stirringstirred for 3 hours
  4. temperatureAfter cooling
  5. customThe yellow solid that formed
  6. filtrationwas filtered
  7. stirringstirred
  8. temperaturein warm dilute ammonium hydroxide
  9. filtrationThe hydroxide solution was filtered
  10. customThe solid obtained upon neutralization
  11. customwas recrystallized from xylene

Sources & evidence

ORD record
ord-cf366f7a41e6443991178e41b7364067
Source dataset
uspto-grants-1976_01
Patent number
US03933849

Reaction notes

Loading…