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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 584849
Notes
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Reaction equation

HRID 584849 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].O1CCCC1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8028TetrahydrofuranHCID 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 8857Ethyl AcetateSolvent

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 separated off and washed with water. The aqueous phase is reextracted with ethyl acetate and the combined organic phases are dried over sodium sulfate and evaporated. The residue is crystallized in 300 ml of methanol at 0° C. The solid is filtered off with suction, washed with cold methanol and dried. 20 g (32%) of the title compound are isolated as a slightly yellow solid (m.p. 103-105° C.).

Workup

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

Sources & evidence

ORD record
ord-91432d61316b4b869423a13c1966f2dc
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06927292B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes