Hydrochloric Acid → HCID 12525897, compound

HRID 441674Notes

Reaction equation

HRID 441674 reaction equation
[C:1]([C:4]1[CH:20]=[CH:19][C:7]2[C:8](=[O:18])[C:9]3[CH:16]=[CH:15][CH:14]=[C:13](Br)[C:10]=3[CH2:11][CH2:12][C:6]=2[CH:5]=1)([OH:3])=[O:2].[ClH:21]>CN1CCCC1=O.O>[C:1]([C:4]1[CH:20]=[CH:19][C:7]2[C:8](=[O:18])[C:9]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:21])[C:10]=3[CH2:11][CH2:12][C:6]=2[CH:5]=1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12525878HCID 12525878, compound

Product 1

HCID 12525897HCID 12525897, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

0.81 G. of 2-carboxy-9-bromo-10,11-dihydro-5-oxo-5H-dibenzo[a,d]cycloheptene and 0.32 g. of cuprous chloride were refluxed for 8 hours in 10 ml of N-methylpyrrolidinone. The solution was cooled and added to a solution of 4.4 g. of ferric chloride hexahydrate in 6 ml of water and 3 ml of concentrated hydrochloric acid. The mixture was heated to 90° for 1 hour, then was poured into water and filtered. The residue was recrystallized from aqueous dimethylformamide to afford 2-carboxy-9-chloro-10,11-dihydro-5-oxo-5H-dibenzo[a,d]cycloheptene, m.p. 258.5°-260°.

Workup

  1. temperatureThe solution was cooled
  2. additionadded to a solution of 4.4 g
  3. temperatureThe mixture was heated to 90° for 1 hour
  4. filtrationfiltered
  5. customThe residue was recrystallized from aqueous dimethylformamide

Sources & evidence

ORD record
ord-01584edecabd4a4198a9c34930b162ab
Source dataset
uspto-grants-1977_08
Patent number
US04041173

Reaction notes

Loading…