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Sodium hydride → Hydrochloric Acid

HRID 1835276
Notes
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Reaction equation

HRID 1835276 reaction equation
[C:1]([NH:4][C:5]([CH2:16][C:17]1[C:22]([CH2:23][Cl:24])=[N:21][CH:20]=[CH:19][N:18]=1)([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[H-].[Na+]>C1COCC1>[C:1]([N:4]1[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:16][C:17]2[C:22](=[N:21][CH:20]=[CH:19][N:18]=2)[CH2:23]1)(=[O:3])[CH3:2].[ClH:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 23503295HCID 23503295, compound

Product 2

HCID 313Hydrochloric AcidYield 85%HCID 9927112Diethyl 6-acetyl-5,6-dihydropyrido[3,4-b]pyrazine-7,7(8H)-dicarboxylateYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1b (1.1 g, 2.36 mmol) in 40 mL THF was added NaH (170 mg, 4.25 mmol, 60% oil dispersion) under N2 and the solution was stirred for 30 min. The reaction was carefully quenched with water and extracted from sat NaHCO33× with EtOAc. The organic layers were dried with MgSO4, filtered, concentrated, and chromatographed on SiO2 using 75% EtOAc in hexane to give 640 mg of 1c as an HCl salt (85% yield). MS found: (M+H)+=322.

Workup

  1. customThe reaction was carefully quenched with water
  2. extractionextracted
  3. dry with materialThe organic layers were dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed on SiO2 using 75% EtOAc in hexane

Sources & evidence

ORD record
ord-450575ba94314880b5a8b5099c0e8354
Source dataset
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06770647B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes