Sodium Carbonate → 1H-Pyrido(4,3-b)indol-1-one, 2,3,4,5-tetrahydro-5-methyl-

HRID 703783Notes

Reaction equation

HRID 703783 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[C:11](=[N:14]O)[CH2:12][CH2:13][C:3]1=2.C(=O)([O-])[O-:17].[Na+].[Na+]>O1CCOCC1>[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[C:11](=[O:17])[NH:14][CH2:12][CH2:13][C:3]1=2

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 6033473,4-Dihydro-4-methylcyclopent[b]indol-1(2H)-one oxime

Product 1

HCID 117902131H-Pyrido(4,3-b)indol-1-one, 2,3,4,5-tetrahydro-5-methyl-

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3,4-Dihydro-4-methylcyclopent[b]indol-1(2H)-one oxime (1.53 g), polyphosphoric acid (40 g) and dioxan (15 ml) were heated at 110°-120° for 2.2h under nitrogen. The reaction mixture was cooled, and treated with 2N sodium carbonate solution (`l). The suspension was extracted with ethyl acetate (4×400 ml) and the combined extracts were dried. Evaporation gave a solid (1.43 g) which was recrystallised from ethyl acetate/cyclohexane. This solid was purified by FCC, eluting with System A (200:10:1) to give a solid (1.26 g) which was recrystallised from ethanol to provide the title compound (960 mg), m.p. 234°-238°.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe suspension was extracted with ethyl acetate (4×400 ml)
  3. customthe combined extracts were dried
  4. customEvaporation

Sources & evidence

ORD record
ord-d76817a2650243778ba293a9cabeb684
Source dataset
uspto-grants-1991_01
Patent number
US04985422

Reaction notes

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