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Hydrochloric Acid → 2-Hydroxyethyl 2-methyl-4-(3-nitrophenyl)-5-oxo-5,7-dihydrofuro(3,4-b)pyridine-3-carboxylate

HRID 615184
Notes
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Reaction equation

HRID 615184 reaction equation
[K].[OH:2][CH2:3][CH2:4][O:5][C:6]([C:8]1[C:9]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)=[C:10]([C:17](O)=[O:18])[C:11]([CH2:15][OH:16])=[N:12][C:13]=1[CH3:14])=[O:7].Cl>O>[CH3:14][C:13]1[N:12]=[C:11]2[CH2:15][O:16][C:17](=[O:18])[C:10]2=[C:9]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)[C:8]=1[C:6]([O:5][CH2:4][CH2:3][OH:2])=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5462222PotassiumHCID 13219263HCID 13219263, compound

Product 1

HCID 132192592-Hydroxyethyl 2-methyl-4-(3-nitrophenyl)-5-oxo-5,7-dihydrofuro(3,4-b)pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

4 g of potassium salt of 2-hydroxymethyl-6-methyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid 5-(2-hydroxyethyl) ester (Example 52) were dissolved in 4 ml of water and acidified with concentrated hydrochloric acid. After standing overnight at room temperature, the mixture was diluted with water, the oil which separated out was extracted with methylene chloride, the organic extracts, after drying over sodium sulphate, were evaporated in vacuo and the residue was recrystallized from isopropanol, melting point 130° C.

Workup

  1. customthe oil which separated out
  2. extractionwas extracted with methylene chloride
  3. dry with materialthe organic extracts, after drying over sodium sulphate
  4. customwere evaporated in vacuo
  5. customthe residue was recrystallized from isopropanol, melting point 130° C.

Sources & evidence

ORD record
ord-242b188dcca04571859c340cb875ea00
Source dataset
uspto-grants-1985_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04497821

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes