Hydrochloric Acid → HCID 21419717, compound

HRID 441672Notes

Reaction equation

HRID 441672 reaction equation
Cl.N1C=CC=CC=1.[C:8]([C:11]1[CH:28]=[CH:27][C:14]2[C:15](=[O:26])[C:16]3[CH:23]=[C:22]([O:24]C)[CH:21]=[CH:20][C:17]=3[CH2:18][CH2:19][C:13]=2[CH:12]=1)([OH:10])=[O:9]>O>[C:8]([C:11]1[CH:28]=[CH:27][C:14]2[C:15](=[O:26])[C:16]3[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][C:17]=3[CH2:18][CH2:19][C:13]=2[CH:12]=1)([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 12525880HCID 12525880, compound

Product 1

HCID 21419717HCID 21419717, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2.2 ml of concentrated hydrochloric acid and 2.0 ml of pyridine which were heated to 220° for 20 minutes, 2.00 g of 2- carboxy-7-methoxy-10,11-dihydro-5-oxo-5H-dibenzo[a,d]cycloheptene was added. The mixture was heated to 210°-215° for 90 minutes, then cooled and diluted with water. The product was filtered off and recrystallized from aqueous ethanol to give 2-carboxy-7-hydroxy-10,11-dihydro-5-oxo-5H-dibenzo[a,d]cycloheptene, m.p. 256°-257°. Similarly, the 8-hydroxy and 9-hydroxy compounds of this invention are obtained from 2-carboxy-8-methoxy-10,11-dihydro-5-oxo-5H-dibenzo[a,d]cycloheptene and 2-carboxy-9-methoxy-10,11-dihydro-5-oxo-5H-dibenzo[a,d]cycloheptene, respectively.

Workup

  1. temperatureThe mixture was heated to 210°-215° for 90 minutes
  2. temperaturecooled
  3. filtrationThe product was filtered off
  4. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-3763d6f3d5314ffab08906e0f48208d5
Source dataset
uspto-grants-1977_08
Patent number
US04041173

Reaction notes

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