Water → 9-(3,3-Diphenylpropoxy)-9H-indeno[1,2-b]pyrazine-2,3(1H, 4H)-dione

HRID 129455Notes

Reaction equation

HRID 129455 reaction equation
[OH:1][CH:2]1[C:14]2[NH:13][C:12](=[O:15])[C:11](=[O:16])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.[C:17]1([CH:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:24][CH2:25]O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[C:17]1([CH:23]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:24][CH2:25][O:1][CH:2]2[C:14]3[NH:13][C:12](=[O:15])[C:11](=[O:16])[NH:10][C:9]=3[C:8]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]2=3)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 299083,3-DiphenylpropanolHCID 190359859-Hydroxy-9H-indeno[1,2-b]pyrazine-2,3(1H,4H)-dione

Product 1

HCID 231940529-(3,3-Diphenylpropoxy)-9H-indeno[1,2-b]pyrazine-2,3(1H, 4H)-dioneYield 12.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of 9-hydroxy-9H-indeno[1,2-b]pyrazine-2,3(1H, 4H)-dione. 1H2O (1.0 g, 4.26 mmol) in benzene (40 ml), 3,3-diphenyl-1-propanol (10 ml) and p-toluensulfonic acid (40 mg) was refluxed with water separation for 48 hours. The reaction mixture was evaporated in vacuo to dryness, the residue was suspended in ethanol (10 ml) and the precipitate was filtered off and washed with ethanol and dried to give 0.224 g (12.5%) of the title compound. M.p. 224°-228° C. 1H-NMR(DMSO-d6, δ): 2.14-2.32 (m, 2H), 3.0-3.22 (m, 2H), 4.13 (t, 1H), 5.22 (s, 1H), 7.0-7.5 (m, 14H), 12.12 (s, 1H), 12.26 (s, 1H).

Workup

  1. customThe reaction mixture was evaporated in vacuo to dryness
  2. filtrationthe precipitate was filtered off
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-e50c8f6a425c49828181deb3f9d61016
Source dataset
uspto-grants-1995_11
Patent number
US05468748

Reaction notes

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