Phosphorus trichloride → 1,2-Dihydro-3-methyl-1-oxo-4-isoquinoline Acetic Acid

HRID 894390Notes

Reaction equation

HRID 894390 reaction equation
O[N:2]1[C:11]([CH3:12])=[C:10]([CH2:13][C:14]([OH:16])=[O:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:17].P(Cl)(Cl)Cl>C(OCC)(=O)C>[CH3:12][C:11]1[NH:2][C:3](=[O:17])[C:4]2[C:9]([C:10]=1[CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 24387Phosphorus trichlorideHCID 127155072-(2-Hydroxy-3-methyl-1-oxoisoquinolin-4-yl)acetic acid

Product 1

HCID 127155091,2-Dihydro-3-methyl-1-oxo-4-isoquinoline Acetic Acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1,2-Dihydro-2-hydroxy-3-methyl-1-oxo-4-isoquinoline acetic acid (4.0 g., 17.2 mmol) dissolved in 30 ml. ethyl acetate at 0° was reacted with phosphorous trichloride (1.50 ml., 17.2 mmol). The mixture was heated at 80° for 1.5 hr then poured onto 100 g. of ice water, stirred for 16 hr and filtered yielding a light yellow crude product; 3.307 mg (89%) mp 280°-295° d. Recrystallization from acetic acid afforded analytically pure material of mp 295°-300° d.

Workup

  1. temperatureThe mixture was heated at 80° for 1.5 hr
  2. additionthen poured onto 100 g
  3. filtrationfiltered

Sources & evidence

ORD record
ord-999185079c1e4b8fa8aefd82cc9b3a95
Source dataset
uspto-grants-1981_08
Patent number
US04283539

Reaction notes

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