Ammonia → 1-Oxo-1,2-dihydroisoquinoline-3-carboxylic acid

HRID 259259Notes

Reaction equation

HRID 259259 reaction equation
[C:1]1([C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]([OH:14])=[O:13])O1)=[O:2].[NH3:15]>C(O)C>[C:1]1([C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]([OH:14])=[O:13])[NH:15]1)=[O:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 3455611-oxo-1H-isochromene-3-carboxylic acid

Product 1

HCID 2800011-Oxo-1,2-dihydroisoquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Isocoumarin -3- carboxylic acid (1.40g.) was added to a solution of ammonia (d. 0.88, 10ml.) in ethanol (40ml.) at 0° and allowed to stand for 24 hours. After removal of solvent in vacuo, 6N hydrochloric acid (70ml.) was added and allowed to stand for 1 hour at 0°. Filtration gave the product as a white solid, mp. 327°-330° (lit mp. 326°-8°), (Found: C, 62.91; H, 3.69; N, 7.46. C10H7NO3 requires C, 63.49; H, 3.73; N, 7.40).

Workup

  1. customAfter removal of solvent in vacuo, 6N hydrochloric acid (70ml.)
  2. additionwas added
  3. waitto stand for 1 hour at 0°
  4. filtrationFiltration

Sources & evidence

ORD record
ord-fc5df54ee5a14b72957d98131e71ba98
Source dataset
uspto-grants-1977_07
Patent number
US04036964

Reaction notes

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