4-Aminopyridine → Carbamic acid, 4-pyridinyl-, phenyl ester

HRID 1182123Notes

Reaction equation

HRID 1182123 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:15]1([O:21][C:22](Cl)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCl>[C:15]1([O:21][C:22](=[O:23])[NH:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 15891Phenyl chloroformate

Product 1

HCID 11401617Carbamic acid, 4-pyridinyl-, phenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4 aminopyridine (0.6 g, 6.37 mmol) in dichloromethane (15 ml) is treated with triethylamine (0.89 ml, 6.37 mmol) followed by phenylchloroformate (0.80 ml, 6.37 mmol) and then stirred at room temperature for 3 days. The reaction mixture is partitioned between dichloromethane and aqueous sodium bicarbonate. The organic phase is dried over magnesium sulphate and evaporated to afford pyridin-4-yl-carbamic acid phenyl ester.

Workup

  1. customThe reaction mixture is partitioned between dichloromethane and aqueous sodium bicarbonate
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-42e4d8d7229d4869922e449fd0836f9c
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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