Ammonia → (2-Amino-6-chloro-3-nitro-pyridin-4-yl)-benzyl-carbamic acid ethyl ester

HRID 639683Notes

Reaction equation

HRID 639683 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[N:5]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:6]1[CH:11]=[C:10]([Cl:12])[N:9]=[C:8](Cl)[C:7]=1[N+:14]([O-:16])=[O:15])[CH3:2].[NH3:25]>C1COCC1>[CH2:1]([O:3][C:4](=[O:24])[N:5]([C:6]1[CH:11]=[C:10]([Cl:12])[N:9]=[C:8]([NH2:25])[C:7]=1[N+:14]([O-:16])=[O:15])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 57856587Benzyl-(2,6-dichloro-3-nitro-pyridin-4-yl)-carbamic acid ethyl ester

Product 1

HCID 57856589(2-Amino-6-chloro-3-nitro-pyridin-4-yl)-benzyl-carbamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl-(2,6-dichloro-3-nitro-pyridin-4-yl)-carbamic acid ethyl ester (500 mg) was dissolved in THF (3 ml) in a ReactiVial. Ammonia (7M in MeOH, 1 ml) was added, the vial was sealed, and the reaction left to stir at RT for 48 h. The reaction mixture was then pre-absorbed directly onto silica and columned on Isco Companion on a silica column (40 g, Redisep), eluting with EtOAc:heptane, increasing the gradient linearly from 10:90 to 40:60 over 10 column volumes. The desired fractions were combined and evaporated to provide the title compound as a yellow gum which solidified on scratching (305 mg)

Workup

  1. customthe vial was sealed
  2. waitthe reaction left
  3. customThe reaction mixture was then pre-absorbed directly onto silica
  4. washeluting with EtOAc
  5. temperatureheptane, increasing the gradient linearly from 10:90 to 40:60 over 10 column volumes
  6. customevaporated

Sources & evidence

ORD record
ord-8919f3c641fb41729ce77b738d9d5e12
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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