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Methanol → HCID 178492956, compound

HRID 2289977
Notes
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Reaction equation

HRID 2289977 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([I:21])=[CH:15][C:14]=3F)=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:27][OH:28].[Cl-].[NH4+]>CN(C=O)C>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([I:21])=[CH:15][C:14]=3[O:28][CH3:27])=[O:9])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 178522917HCID 178522917, compound

Product 1

HCID 178492956HCID 178492956, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
135 °C

Procedure

N-(4-Chlorobenzyl)-8-fluoro-4-hydroxy-6-iodo-3-quinolinecarboxamide (2.95 g) from Example No. 5 and sodium hydride (60% dispersion, 520 mg) is suspended in DMF (60 mL) and to the mixture is added methanol (288 μL). After being heated for 1 h at 135° C., additional sodium hydride (200 mg) is added, and the mixture is heated for an additional 1 h. The reaction mixture is allowed to cool to rt and then is poured into saturated aqueous ammonium chloride (200 mL). The resulting precipitate is filtered and washed with water (20 mL), tert-butyl methyl ether (20 mL), and heptane (20 mL). The crude product is purified by column chromatography (heptane/2-propanol, 9/1; 4/1) to afford 1.68 g (56%) of the title compound as a white solid. Recrystallization (acetic acid, water) affords a hydrate (1H2O).

Workup

  1. temperaturethe mixture is heated for an additional 1 h
  2. temperatureto cool to rt
  3. filtrationThe resulting precipitate is filtered
  4. washwashed with water (20 mL), tert-butyl methyl ether (20 mL), and heptane (20 mL)
  5. customThe crude product is purified by column chromatography (heptane/2-propanol, 9/1; 4/1)

Sources & evidence

ORD record
ord-f51222277b4748c4a24c20a35970da2a
Source dataset
uspto-grants-2000_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06093732

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes