Citric Acid → HCID 22253012, compound

HRID 1612465Notes

Reaction equation

HRID 1612465 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:5]=[C:4]([O:15][CH3:16])[N:3]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[CH2:30]([NH:37][CH2:16][O:15][C:4]1[CH:5]=[C:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:7]=[CH:2][N:3]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 3

HCID 311Citric AcidHCID 7504BenzylamineHCID 22253007HCID 22253007, compound

Product 1

HCID 22253012HCID 22253012, compound

Procedure

t-Butyl 2-chloro-6-methoxypyridine-4-carboxylate (1.0 g) (D60) was heated in benzylamine (20 mL) for 16.5 h at 140° C. After cooling, the mixture was poured into citric acid solution (10% aq.) and extracted twice with ether. The combined extracts were washed with water and brine, dried (MgSO4) and evaporated to a yellow gum. This was chromatographed on silica, eluting with hexane/ether, giving the title compound (D54) as an off-white solid (0.411 g).

Workup

  1. temperatureAfter cooling
  2. extractionextracted twice with ether
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to a yellow gum
  6. customThis was chromatographed on silica
  7. washeluting with hexane/ether

Sources & evidence

ORD record
ord-5c95f1ef0c954de3bbf899efd823bfb0
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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