Methanol → HCID 68483231, compound

HRID 1874980Notes

Reaction equation

HRID 1874980 reaction equation
[C:1]([C:4]1[NH:8][C:7]([C:9]([O:11]C)=[O:10])=[C:6]([Cl:13])[CH:5]=1)(=[O:3])[CH3:2].CO.[Li+].[OH-]>C1COCC1>[C:1]([C:4]1[NH:8][C:7]([C:9]([OH:11])=[O:10])=[C:6]([Cl:13])[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 68487863HCID 68487863, compound

Product 1

HCID 68483231HCID 68483231, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 5-acetyl-3-chloro-1H-pyrrole-2-carboxylate (0.034 g, 0.169 mmol) was dissolved in THF (1 mL), methanol (1 mL) and 1N LiOH (1 mL). The reaction mixture was heated to 60° C. and stirred. The reaction mixture was evaporated and purification was accomplished by reverse-phase HPLC (water/acetonitrile with 0.1% TFA) to afford the title compound (0.030 g, 76%) as an impure product which was used with no further purification. LCMS: m/z 186.0 (M−1).

Workup

  1. customThe reaction mixture was evaporated
  2. custompurification

Sources & evidence

ORD record
ord-5db6906e9bd64284a0217ba121fb386f
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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