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Methyl 5-(4-methoxy-3-nitrophenyl)-3-pyridinecarboxylate → HCID 19837271, compound

HRID 477048
Notes
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Reaction equation

HRID 477048 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][CH:12]=[C:13]([CH:18]=2)[C:14]([O:16][CH3:17])=[O:15])=[CH:5][C:4]=1[N+:19]([O-])=O>C(OCC)(=O)C.[C].[Pd]>[NH2:19][C:4]1[CH:5]=[C:6]([C:9]2[CH:10]=[N:11][CH:12]=[C:13]([CH:18]=2)[C:14]([O:16][CH3:17])=[O:15])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 14769996Methyl 5-(4-methoxy-3-nitrophenyl)-3-pyridinecarboxylate2×

Product 1

HCID 19837271HCID 19837271, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

990 mg of the resulting nitro compound was dissolved in 60 ml of ethyl acetate, and 0.3 g of 10% palladium-carbon was added. The nitro compounds was thus catalytically reduced with stirring at 50° C. The catalyst was removed in a customary manner, and the resulting yellow crystals were recrystallized from methylene chloride-ether to give 723 mg (yield 81%) of methyl 5-(3-amino-4-methoxyphenyl)nicotinate as pale yellow needles having a melting point of 98° to 99° C.

Workup

  1. customThe catalyst was removed in a customary manner
  2. customthe resulting yellow crystals were recrystallized from methylene chloride-ether

Sources & evidence

ORD record
ord-82c4dd22dec043b6ac03a755302ac152
Source dataset
uspto-grants-1989_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04886822

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes