Pyridine → HCID 20587814, compound

HRID 413267Notes

Reaction equation

HRID 413267 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.N1C=CC=CC=1.[C:15]1([O:21][C:22](Cl)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[C:15]1([O:21][C:22](=[O:23])[NH:8][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 153482-Amino-5-methylpyridineHCID 15891Phenyl chloroformate

Product 1

HCID 20587814HCID 20587814, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring mixture of 5-methyl-pyridin-2-ylamine (1.0 g, 9.25 mmol) and pyridine (20 ml) in dry CH2Cl2 add phenylchloroformate (2.2 g, 13.9 mmol) and stir for 24 hours at room temperature. Add water and a solution of 1:1 EtOAc/hexanes and separate the organic layer. Wash the organic layer with 1N HCl three times and with brine once. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo. Purify by flash column chromatography (0-10% EtOAc/CH2Cl2) to obtain (5-methyl-pyridin-2-yl)-carbamic acid phenyl ester. Mass spec.: M+1=229 (AP+).

Workup

  1. customAdd water and a solution of 1:1 EtOAc/hexanes and separate the organic layer
  2. washWash the organic layer with 1N HCl three times
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customPurify by flash column chromatography (0-10% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-d4698279a0eb4fc2910109e17eee6c68
Source dataset
uspto-grants-2003_05
Patent number
US06566367B2

Reaction notes

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