HCID 73843873, compound → HCID 135818870, compound

HRID 2418307Notes

Reaction equation

HRID 2418307 reaction equation
CC1C=CC(N[N:9]=[C:10]2[C:15]3=[N:16][C:17]4[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=4[C:23](=[O:24])[N:14]3[CH:13]([CH3:25])[CH2:12][CH2:11]2)=CC=1>O>[CH3:25][CH:13]1[N:14]2[C:15](=[N:16][C:17]3[CH2:18][CH2:19][CH2:20][CH2:21][C:22]=3[C:23]2=[O:24])[C:10]2[NH:9][C:19]3[C:20]([C:11]=2[CH2:12]1)=[CH:21][C:22]([CH3:23])=[CH:17][CH:18]=3

Participants

3

Reactant 1

HCID 73843873HCID 73843873, compound

Product 1

HCID 135818870HCID 135818870, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

1 g of 6-(4-Methyl-phenylhydrazono)-9-methyl-1,2,3,4,6,7,8,9-octahydro-pyrido[2,1-b]quinazoline-11-one is added to 10 g of polyphosphoric acid heated to 180° C. and the reaction mixture is heated for 40 minutes at this temperature. After cooling the mixture is diluted with 60 ml of water. A yellowish-white crystalline precipitate is obtained which is filtered and washed with water. After drying the obtained solid is dissolved in chloroform and the undissolved part is filtered off. The solution is treated with active charcoal and evaporated. The obtained yellowish-white oil is crystallized from ethyl acetate. 0.4 g of 7,10-dimethyl-5-oxo-1,2,3,4,7,8-hexahydro-5H,13H-indolo[2',3';3,4]pyrido[2,1-b]quinazoline are obtained melting at 220° C.

Workup

  1. temperaturethe reaction mixture is heated for 40 minutes at this temperature
  2. temperatureAfter cooling the mixture
  3. customA yellowish-white crystalline precipitate is obtained which
  4. filtrationis filtered
  5. washwashed with water
  6. customAfter drying the obtained solid
  7. dissolutionis dissolved in chloroform
  8. filtrationthe undissolved part is filtered off
  9. additionThe solution is treated with active charcoal
  10. customevaporated
  11. customThe obtained yellowish-white oil is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-4f0e389f0c034d2ba6afcb4c9bc26ac5
Source dataset
uspto-grants-1984_09
Patent number
US04472399

Reaction notes

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