Dimethylformamide → HCID 23467880, compound

HRID 443545Notes

Reaction equation

HRID 443545 reaction equation
P(Cl)(Cl)([Cl:3])=O.CN(C)[CH:8]=[O:9].[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:21][C:20](=O)[NH:19]2)[CH:15]=[CH:16][CH:17]=1.[OH-].[Na+]>O1CCCC1.C1(C)C=CC=CC=1>[Cl:3][C:20]1[N:19]=[C:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([Cl:11])[CH:13]=2)[C:27]2[C:22]([C:21]=1[CH:8]=[O:9])=[CH:23][CH:24]=[CH:25][CH:26]=2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 4562359HCID 4562359, compound

Product 1

HCID 23467880HCID 23467880, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

199 g of phosphorus oxichloride are added dropwise to a solution of 99 g of N,N-dimethyl formamide in 400 ml of tetrahydrofuran at a rate such that the temperature does not exceed 5° C. Stirring is continued for 20 minutes at room temperature. Next, 87.7 g of 1-(3-chlorophenyl)-1,4-dihydro-3-(2H)-isoquinolinone are added in portions at 0° C. After a 2 hour stirring at 0° to 5° C., the reaction solution is poured into a mixture of 1.95 l of 2N NaOH, 6 kg of ice and 1 l of toluene. The toluene phase is separated, washed twice with water and added to 1.3 l of acetone and 1.3 l of 2N H2SO4. 38.8 g of carefully pulverized potassium permanganate are added in portions and at 20° C. to the heterogeneous mixture obtained and the mixture is stirred for 6 hours. The toluene phase is separated, washed successively with water, 2N NaOH and again with water, dried, filtered and the solvent is removed under reduced pressure.

Workup

  1. customdoes not exceed 5° C
  2. stirringAfter a 2 hour stirring at 0° to 5° C.
  3. customThe toluene phase is separated
  4. washwashed twice with water
  5. additionadded to 1.3 l of acetone and 1.3 l of 2N H2SO4
  6. addition38.8 g of carefully pulverized potassium permanganate are added in portions and at 20° C. to the heterogeneous mixture
  7. customobtained
  8. stirringthe mixture is stirred for 6 hours
  9. customThe toluene phase is separated
  10. washwashed successively with water, 2N NaOH and again with water
  11. customdried
  12. filtrationfiltered
  13. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-00b27e40b15047afbab2f37858bef745
Source dataset
uspto-grants-1981_04
Patent number
US04260763

Reaction notes

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