Diisopropylethylamine → Methyl 5-{[(4-nitrophenoxy)carbonyl]oxy}nicotinate

HRID 2074307Notes

Reaction equation

HRID 2074307 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][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([CH:24]=1)[C:20]([O:22][CH3:23])=[O:21].C(N(C(C)C)CC)(C)C>ClCCl>[N+:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][C:2]([O:14][C:15]2[CH:16]=[N:17][CH:18]=[C:19]([CH:24]=2)[C:20]([O:22][CH3:23])=[O:21])=[O:3])=[CH:6][CH:7]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 354317Methyl 5-hydroxypyridine-3-carboxylate

Product 1

HCID 57421835Methyl 5-{[(4-nitrophenoxy)carbonyl]oxy}nicotinateYield 76.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Nitrophenyl chloroformate (7.0 g) was added to a dichloromethane (100 ml) solution of methyl 5-hydroxynicotinate (5.3 g) and diisopropylethylamine (6.1 ml), followed by stirring at room temperature for 1 hour. The reaction liquid was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting solid was washed with EtOAc/hexane and dried under reduced pressure to obtain methyl 5-{[(4-nitrophenoxy)carbonyl]oxy}nicotinate (8.4 g).

Workup

  1. customThe reaction liquid
  2. washwas washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. washthe resulting solid was washed with EtOAc/hexane
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-dec9c4ca452b45bbbbc11ad1ca7e89a2
Source dataset
uspto-grants-2011_04
Patent number
US07919495B2

Reaction notes

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