Ammonia → Methyl 5-(aminocarbonyl)-3-chloro-1H-pyrrole-2-carboxylate

HRID 1874967Notes

Reaction equation

HRID 1874967 reaction equation
[NH3:1].[Cl:2][C:3]1[CH:7]=[C:6]([C:8](Cl)=[O:9])[NH:5][C:4]=1[C:11]([O:13][CH3:14])=[O:12]>C1COCC1>[NH2:1][C:8]([C:6]1[NH:5][C:4]([C:11]([O:13][CH3:14])=[O:12])=[C:3]([Cl:2])[CH:7]=1)=[O:9]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86644903Methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 68481017Methyl 5-(aminocarbonyl)-3-chloro-1H-pyrrole-2-carboxylateYield 51.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ammonia (5.8 mL, 2.9 mmol) was added to a solution of methyl 3-chloro-5-(chlorocarbonyl)-1H-pyrrole-2-carboxylate (0.15 g, 0.58 mmol) in THF and the resulting solution stirred until no starting material was evident by TLC. The solvent was evaporated and purification was accomplished by silica gel column chromatography (30 to 100% EtOAc/hexanes) to afford the title compound (0.060 g, 51%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.29 (br. s., 1H), 7.82 (br. s., 1H), 7.47 (br. s., 1H), 6.80 (s, 1H), 3.77 (s, 3H). LCMS: m/z 201.4 (M−1).

Workup

  1. customThe solvent was evaporated
  2. custompurification

Sources & evidence

ORD record
ord-208b14809594490db9757216793c72ec
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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