1-Chloro-4-(chloromethyl)benzene → HCID 22923790, compound

HRID 2258305Notes

Reaction equation

HRID 2258305 reaction equation
[OH:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1>>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][O:1][C:2]2[C:3]([C:8]([O:10][CH2:18][C:17]3[CH:20]=[CH:21][C:14]([Cl:13])=[CH:15][CH:16]=3)=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 134013-Hydroxypicolinic AcidHCID 24758Sodium hydride

Product 1

HCID 22923790HCID 22923790, compound

Procedure

8.4 g (60 mmol) of 3-hydroxypyridine-2-carboxylic acid were alkylated (3 h, 110° C.) with 5.2 g (approximately 130 mmol, 60%) of sodium hydride and 19.3 g (120 mmol) of 4-chlorobenzyl chloride in N,N-dlmethylacetamide in analogy with Example 30a). After concentration in vacuo and extraction with Na bicarbonate solution, the residue was purified on silica gel using heptane/ethyl acetate (1:1), and 14.8 g of the product were crystallized from appropriate fractions using diisopropyl ether, m.p. 92°-94° C.

Workup

  1. custom(3 h, 110° C.)
  2. concentrationAfter concentration
  3. extractionin vacuo and extraction with Na bicarbonate solution
  4. customthe residue was purified on silica gel
  5. customwere crystallized from appropriate fractions

Sources & evidence

ORD record
ord-e36a5ea2179d4c99a2f7359a664ecf92
Source dataset
uspto-grants-1997_08
Patent number
US05658933

Reaction notes

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