Water → HCID 13827288, compound

HRID 978658Notes

Reaction equation

HRID 978658 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[Br-].[O:13]=[C:14]1[C:23]2[C:18](=[CH:19][C:20]([CH2:24][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:21][CH:22]=2)[CH:17]=[N:16][NH:15]1.O>CS(C)=O>[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6](/[CH:7]=[CH:24]\[C:20]2[CH:19]=[C:18]3[C:23](=[CH:22][CH:21]=2)[C:14](=[O:13])[NH:15][N:16]=[CH:17]3)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 74794-(Dimethylamino)BenzaldehydeHCID 20203491HCID 20203491, compound

Product 1

HCID 13827288HCID 13827288, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

4-dimethylaminobenzaldehyde (9 gm) in DMSO (30 ml) was added to a solution of 1-oxo-2H-phthalazin-6-ylmethyl triphenylphosphonium bromide (0.04 mole) in DMSO (100 ml) and stirred overnight at room temperature. The reaction mixture was added to water (1 L), stirred, and the precipitate was filtered to give a solid. The solid was air dried, slurried with acetone (200 ml) and filtered and dried to give a mixture of cis and trans isomers (9.9 gm). The solid was recrystallized from DMF (65 ml) and filtered to give pure cis product (4.8 gm), mp=312°-318° C.

Workup

  1. stirringstirred
  2. filtrationthe precipitate was filtered
  3. customto give a solid
  4. customdried
  5. filtrationfiltered
  6. customdried
  7. customto give
  8. additiona mixture of cis and trans isomers (9.9 gm)
  9. customThe solid was recrystallized from DMF (65 ml)
  10. filtrationfiltered

Sources & evidence

ORD record
ord-ceae80c923154b4190fc54995983532c
Source dataset
uspto-grants-1987_05
Patent number
US04665181

Reaction notes

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