Sodium Hydroxide → 3,4-Dihydrobenzo[c][1,5]naphthyridin-2(1H)-one

HRID 1906454Notes

Reaction equation

HRID 1906454 reaction equation
[CH2:1]1[CH:13]2[N:4]([CH2:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:12]2=O)[C:3](=[N:15]O)[CH2:2]1.[OH-:17].[Na+]>C(OCC)(=O)C>[NH:15]1[C:3](=[O:17])[CH2:2][CH2:1][C:13]2[N:4]=[CH:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:12]1=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 736637961,10a-Dihydropyrrolo[1,2-b]isoquinoline-3,10[2H,5H]-dione oxime

Product 1

HCID 136625093,4-Dihydrobenzo[c][1,5]naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 300 g of vigorously stirred polyphosphoric acid warmed to 115° C., 10 g of 1,10a-dihydropyrrolo[1,2-b]isoquinoline-3,10[2H,5H]-dione oxime was added. The mixture was held at this bath temperature for 10 minutes. The internal temperature rose to 135°-140° C. The mixture was then poured into 1500 ml of ice water, and the mixture was basified with 50% NaOH to about pH=8 and the resultant crystalline precipitate was collected to give 7.14 g of crude product Chromatography on a silica gel column, using ethyl acetate gave 4.8 g of pure product, m.p. 225° C.

Workup

  1. customThe mixture was held at this bath
  2. customrose to 135°-140° C
  3. customthe resultant crystalline precipitate was collected
  4. customto give 7.14 g of crude product Chromatography on a silica gel column

Sources & evidence

ORD record
ord-075e7bb6ed594bfb8e8145b86791b868
Source dataset
uspto-grants-1987_03
Patent number
US04652567

Reaction notes

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