Methanol → HCID 18461360, compound

HRID 2303837Notes

Reaction equation

HRID 2303837 reaction equation
COC[O:4][C:5]1[C:22]([CH3:23])=[CH:21][C:8]([O:9][C:10]2[N:15]=[C:14]([NH:16][CH3:17])[C:13]([N+:18]([O-])=O)=[CH:12][CH:11]=2)=[C:7]([CH3:24])[C:6]=1[CH3:25].CO.[O:28]1CC[CH2:30][CH2:29]1>[Pd]>[OH:28][CH2:29][C:30]1[N:16]([CH3:17])[C:14]2=[N:15][C:10]([O:9][C:8]3[CH:21]=[C:22]([CH3:23])[C:5]([OH:4])=[C:6]([CH3:25])[C:7]=3[CH3:24])=[CH:11][CH:12]=[C:13]2[N:18]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 8028TetrahydrofuranHCID 18461369HCID 18461369, compound

Product 1

HCID 18461360HCID 18461360, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

A mixture of 288 g of 6-(4-methoxymethoxy-2,3,5-trimethylphenoxy)-2-methylamino-3-nitropyridine, 14 g of 10% palladium on carbon and 1500 ml of methanol was stirred at room temperature for 2 hours under a hydrogen atmosphere. To the reaction mixture, 14 g of 10% palladium on carbon, 500 ml of methanol and 500 ml of tetrahydrofuran were added and the resulting mixture was stirred at 50° C. for 8 hours under a hydrogen atmosphere. The palladium on carbon in the reaction mixture was filtered off and the filtrate was concentrated by evaporation. To the residue, 500 g of glycolic acid were added and the mixture was stirred at 150° C. for 6 hours. To the reaction mixture, 1000 ml of a 4N aqueous hydrochloric acid solution were added and the mixture was stirred at 120° C. for one hour. The reaction mixture was allowed to stand overnight at room temperature. The reaction mixture was poured into iced water, followed by neutralization with an aqueous sodium hydroxide solution and an aqueous sodium carbonate solution. The resulting solid substance was separated by filtration and purified by chromatography through a silica gel column with tetrahydrofuran as an eluting solvent. The resulting solid substance from the eluate was washed with ethanol, whereby 45.5 g of the title compound were obtained.

Workup

  1. stirringthe resulting mixture was stirred at 50° C. for 8 hours under a hydrogen atmosphere
  2. filtrationThe palladium on carbon in the reaction mixture was filtered off
  3. concentrationthe filtrate was concentrated by evaporation
  4. additionTo the residue, 500 g of glycolic acid were added
  5. stirringthe mixture was stirred at 150° C. for 6 hours
  6. additionTo the reaction mixture, 1000 ml of a 4N aqueous hydrochloric acid solution were added
  7. stirringthe mixture was stirred at 120° C. for one hour
  8. waitto stand overnight at room temperature
  9. additionThe reaction mixture was poured into iced water
  10. customThe resulting solid substance was separated by filtration
  11. custompurified by chromatography through a silica gel column with tetrahydrofuran as an eluting solvent
  12. washThe resulting solid substance from the eluate was washed with ethanol

Sources & evidence

ORD record
ord-dc1334d25b9e4ee9af418697f308a34c
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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