Phosphorus oxychloride → 4-Chloro-1-furan-2-ylmethyl-6-methoxy-phthalazine

HRID 2268924Notes

Reaction equation

HRID 2268924 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10](=O)[NH:9][N:8]=1.O=P(Cl)(Cl)[Cl:22]>C(#N)C>[Cl:22][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[C:7]([CH2:6][C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[N:8][N:9]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 183816674-Furan-2-ylmethyl-7-methoxy-2H-phthalazin-1-one

Product 1

HCID 121090664-Chloro-1-furan-2-ylmethyl-6-methoxy-phthalazineYield 89.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension under N2 of 4-furan-2-ylmethyl-7-methoxy-2H-phthalazin-1-one (1.8 g, 7.02 mmoles), prepared as described in example 126, in acetonitrile (40 ml) was added under stirring with POCl3 (3.27 ml, 35.1 mmoles), and refluxed for 1 hour, then dried. The residue was suspended in water (50 ml), added with NaHCO3 up to alkalinity, and stirred for 30 minutes, then extracted in CH2Cl2. The organic phase was anhydrified over Na2SO4 and dried to give a residue which was taken up in petrolatum and filtered. The resultant solid was dried under vacuum at 40° C. to give 1.72 g of the title compound (yield: 89%).

Workup

  1. additionwas added
  2. temperaturerefluxed for 1 hour
  3. customdried
  4. additionadded with NaHCO3 up to alkalinity
  5. extractionextracted in CH2Cl2
  6. customdried
  7. customto give a residue which
  8. filtrationfiltered
  9. customThe resultant solid was dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-be1addcc4a3c4a41803246b8eec72d2c
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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