Pyridine → 4-Nitrophenyl hydrogen carbonimidate

HRID 1830704Notes

Reaction equation

HRID 1830704 reaction equation
[N:1]1C=CC=CC=1.Cl[C:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)=[O:9]>ClCCl>[C:8](=[O:9])([O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)[NH2:1]

Participants

4

Reactant 2

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 1699564-Nitrophenyl hydrogen carbonimidateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred, cooled (about 0° C.) solution of methyl-3-amino-4-methoxy benzoate (5.0 g; 27.6 mmol) in dry dichloromethane (175 mL) was added pyridine (2.34 mL; 29 mmol) followed by 4-nitrophenyl chloroformate (5.8 9; 29 mmol) under a nitrogen (N2) atmosphere. After stirring for 8 hours, the, reaction was washed with 2N aqueous hydrochloric acid (2×200 mL), saturated aqueous sodium bicarbonate (2×200 mL), and brine (200 mL), then dried (MgSO4), and filtered. The filtered solution was diluted with ethyl acetate and hexanes (about 800 mL) until a precipitate formed. The solid was collected on a Buchner funnel with suction, and air dried to provide the desired carbamate as a white solid (70% yield).

Workup

  1. customthe, reaction
  2. washwas washed with 2N aqueous hydrochloric acid (2×200 mL), saturated aqueous sodium bicarbonate (2×200 mL), and brine (200 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. additionThe filtered solution was diluted with ethyl acetate and hexanes (about 800 mL) until a precipitate
  6. customformed
  7. customThe solid was collected on a Buchner funnel with suction, and air
  8. customdried

Sources & evidence

ORD record
ord-38090de1332c4e7ab9b704f2e851d6a3
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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