4-Hydroxymethylpyridine → HCID 14725098, compound

HRID 1586649Notes

Reaction equation

HRID 1586649 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[OH:14][CH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:2](=[O:3])([O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)[O:14][CH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 114724-HydroxymethylpyridineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 14725098HCID 14725098, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

20.3 g of p-nitrophenyl chloroformate were dissolved in 150 ml of CH2Cl2 (absolute) and the solution was cooled to 0° C. under N2. 520 mg of 4-dimethylaminopyridine (DMAP) were added and 10 g of 4-hydroxymethylpyridine in 50 ml of CH2Cl2 (absolute) were then added dropwise to this solution. The mixture was stirred overnight at R.T. and the crystals which had precipitated were filtered off. The crystals were recrystallized using fresh CH2Cl2 under the influence of heat and, after cooling, were filtered off again.

Workup

  1. customthe crystals which had precipitated
  2. filtrationwere filtered off
  3. customThe crystals were recrystallized
  4. temperatureof heat
  5. temperatureafter cooling
  6. filtrationwere filtered off again

Sources & evidence

ORD record
ord-7efb2ec7610e471d85e735766a4ff50a
Source dataset
uspto-grants-1993_06
Patent number
US05215968

Reaction notes

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