Potassium Carbonate → HCID 22165450, compound

HRID 2352359Notes

Reaction equation

HRID 2352359 reaction equation
C([N:4]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[C:9]2[C:15]([Cl:19])=[CH:16][CH:17]=[CH:18][C:8]=2[CH2:7][CH2:6][C:5]1=[O:20])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:19][C:15]1[C:9]2[C:10](=[O:14])[CH2:11][CH2:12][CH2:13][NH:4][C:5](=[O:20])[CH2:6][CH2:7][C:8]=2[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 19833137HCID 19833137, compound

Product 1

HCID 22165450HCID 22165450, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

7.60 g of 4-acetyl-9-chloro-1,2,4,5,6,7-hexahydro-4-benzazecine-3,8-dione were dissolved in 240 ml of methanol and treated with a mixture of 36 ml of methanol and 4 ml of saturated potassium carbonate solution. The mixture was stirred at room temperature for 1 hour and thereafter the solvent was removed in vacuo. The residue was triturated in ethyl acetate. The crystallized-out 9-chloro-1,2,4,5,6,7-hexahydro-4-benzazecine-3,8-dione was filtered off and exhibited a melting point of 211°-214°. The filtrate was chromatographed on 100 g of silica gel (particle size 0.2-0.5 mm). A further portion of 9-chloro-1,2,4,5,6,7-hexahydro-4-benzazecine-3,8-dione can be isolated from the ethyl acetate eluate.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was triturated in ethyl acetate
  3. filtrationThe crystallized-out 9-chloro-1,2,4,5,6,7-hexahydro-4-benzazecine-3,8-dione was filtered off
  4. customThe filtrate was chromatographed on 100 g of silica gel (particle size 0.2-0.5 mm)

Sources & evidence

ORD record
ord-5936cb6053664bbdb812aebc8e0a12ee
Source dataset
uspto-grants-1989_10
Patent number
US04876340

Reaction notes

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