2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → (9S)-2,3-Dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

HRID 2249712Notes

Reaction equation

HRID 2249712 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:13]3[NH:12][C@H:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:10][C:9](=[O:20])[C:8]=3[CH2:7][CH2:6][N:5]2[C:21]=1[CH3:22].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[OH-].[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.O1CCCC1>[CH3:1][C:2]1[N:3]=[C:4]2[C:13]3[NH:12][C@H:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:10][C:9](=[O:20])[C:8]=3[CH:7]=[CH:6][N:5]2[C:21]=1[CH3:22]

Participants

7

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 69288840(9S)-2,3-Dimethyl-9-phenyl-5,6,7,8,9,10-hexahydroimidazo[1,2-h][1,7]naphthyridin-7-one

Product 1

HCID 69291849(9S)-2,3-Dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-oneYield 32%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

63.5 g (0.22 mol) of (9S)-2,3-dimethyl-9-phenyl-5,6,7,8,9,10-hexahydroimidazo[1,2-h][1,7]naphthyridin-7-one are dissolved in 250 ml of toluene and 250 ml of tetrahydrofuran, and cooled to 0° C. 59 g (0.26 mol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone are introduced in portions of 10 g over a period of 1 h with mechanical stirring. The reaction mixture is stirred at room temperature for 16 h. 1.2 l of 0.5 N sodium hydroxide solution and 1 l of ethyl acetate are then added dropwise. The organic phase is removed and washed with water. The aqueous phase is reextracted with ethyl acetate, and the combined organic phases are dried over sodium sulphate and evaporated. The residue is crystallized at 0° C. in 300 ml of methanol. The solid is filtered off with suction, washed with cold methanol and dried. 20 g (32%) of the title compound are isolated as a pale yellow solid (m.p. 103-105° C.).

Workup

  1. customThe organic phase is removed
  2. washwashed with water
  3. dry with materialthe combined organic phases are dried over sodium sulphate
  4. customevaporated
  5. customThe residue is crystallized at 0° C. in 300 ml of methanol
  6. filtrationThe solid is filtered off with suction
  7. washwashed with cold methanol
  8. customdried

Sources & evidence

ORD record
ord-f87e1c4ba3d54de1966ac8dc96310b90
Source dataset
uspto-grants-2008_01
Patent number
US07314935B2

Reaction notes

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