p-Toluenesulfonic acid → 5,6-dihydro-3-methoxy-12-phenylnaphtho[1,2-b][1,8]naphthyridin-7(12H)-one

HRID 1193746Notes

Reaction equation

HRID 1193746 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[CH2:8][CH2:7][CH2:6]2.[C:14]1([NH:20][C:21]2[N:30]=[CH:29][CH:28]=[CH:27][C:22]=2[C:23](OC)=[O:24])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:9]3[N:20]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:21]4[C:22]([C:23](=[O:24])[C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=1)=[CH:27][CH:28]=[CH:29][N:30]=4

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 141126-Methoxy-alpha-tetraloneHCID 10998755Methyl 2-anilinopyridine-3-carboxylate

Product 1

HCID 144232745,6-dihydro-3-methoxy-12-phenylnaphtho[1,2-b][1,8]naphthyridin-7(12H)-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

For example, with 3,4-dihydro-6-methoxy-1-naphthalenone as the ketone and methyl 2-phenylaminonicotinate as the arylaminonicotinate, the 1,3-diketone,3,4-dihydro-6-methoxy-2-[[2-(phenylamino)-3-pyridinyl]-carbonyl]-1(2H)-napthalenone, results from the process of Example 8. To cyclize, reflux 9 g of the diketone in 400 ml of toluene containing a catalytic amount of p-toluenesulfonic acid. Collect the evolved water in a Dean-Stark trap. Remove the heat after 21/2 hours and allow the mixture to stand overnight. Distill the toluene under vacuum on a steam bath and crystallize the residue from acetonitrile, to provide the product 5,6-dihydro-3-methoxy-12-phenylnaphtho[1,2-b][1,8]naphthyridin-7(12H)-one, m.p. 234°-237.5° C., after crystallization from CH3CN.

Workup

  1. customCollect the evolved water in a Dean-Stark trap
  2. customRemove the
  3. temperatureheat after 21/2 hours
  4. distillationDistill the toluene under vacuum on a steam bath
  5. customcrystallize the residue from acetonitrile

Sources & evidence

ORD record
ord-2e9e7300cf0c408c9f05f73be992bfc6
Source dataset
uspto-grants-1989_03
Patent number
US04810708

Reaction notes

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