Phosphorus oxychloride → 5-Benzyloxy-1-chloro-6-methoxy-phthalazine

HRID 2268879Notes

Reaction equation

HRID 2268879 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[N:12][NH:13][C:14]2=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:24]>C(#N)C>[CH2:1]([O:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[N:12][N:13]=[C:14]2[Cl:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 183746425-Benzyloxy-6-methoxy-2H-phthalazin-1-one

Product 1

HCID 183816095-Benzyloxy-1-chloro-6-methoxy-phthalazineYield 97.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 5-benzyloxy-6-methoxy-2H-phthalazin-1-one (4 g, 14.17 mmoles), prepared as described in example 69, in acetonitrile (40 ml), and POCl3 (6.5 ml, 70.8 mmoles) was heated at 80° C. under stirring up to dissolution. After 30 minutes the solution was evaporated and the residue taken up in CH2Cl2 (100 ml), washed with a cold solution of NaOH (20 ml) and water (200 ml) and extracted in ethyl ether (twice) and ethyl acetate (once) checking the pH to be around 7. The organic phase was washed with a saturated NaCl solution, anhydrified and concentrated to give 4.15 g of the title compound (yield: 97%).

Workup

  1. customprepared
  2. customAfter 30 minutes the solution was evaporated
  3. washwashed with a cold solution of NaOH (20 ml) and water (200 ml)
  4. extractionextracted in ethyl ether (twice) and ethyl acetate (once)
  5. washThe organic phase was washed with a saturated NaCl solution
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8ba76828ca56450699b2f76f4e1bd173
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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