Phosphorus oxychloride → Methyl 1-chloro-4-hydroxyisoquinoline-3-carboxylate

HRID 2289833Notes

Reaction equation

HRID 2289833 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=O)[NH:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14].P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([OH:1])=[C:3]([C:13]([O:15][CH3:16])=[O:14])[N:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 788106Methyl 4-hydroxy-1-oxo-1,2-dihydroisoquinoline-3-carboxylate

Product 1

HCID 18698155Methyl 1-chloro-4-hydroxyisoquinoline-3-carboxylate

Procedure

2.84 g (13 mmol) of methyl 4-hydroxy-1 (2H)-isoquinolone-3-carboxylate (prepared as in M. Suzuki, SYNTHESIS, 461 (1978)) was stirred at 70° C. for 3 h in 25 ml of phosphorus oxychloride. After cooling, the mixture was added to 500 ml of ice water, the precipitate was filtered off with suction next morning and dried at 70° C. under an IR Lamp. 2.96 g of product were obtained; m.p. 168° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered off with suction next morning
  3. customdried at 70° C. under an IR Lamp

Sources & evidence

ORD record
ord-5500c18e52434059900a9d76026a546c
Source dataset
uspto-grants-2000_07
Patent number
US06093730

Reaction notes

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