Hydrochloric Acid → HCID 67366909, compound

HRID 1753126Notes

Reaction equation

HRID 1753126 reaction equation
[OH-].[Li+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:21])[CH2:11][N:12]2[CH:16]=[CH:15][CH:14]=[C:13]2[C:17]([O:19]C)=[O:18])=[CH:6][CH:5]=1.Cl>C1COCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:21])[CH2:11][N:12]2[CH:16]=[CH:15][CH:14]=[C:13]2[C:17]([OH:19])=[O:18])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 13154205HCID 13154205, compound

Product 1

HCID 67366909HCID 67366909, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (116.73 mg, 2.15 mmol) was added to a solution of methyl 1-[2-(4-chlorophenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylate (515 mg, 1.85 mmol) in THF (9 mL) water (1 mL) and stirred at room temperature overnight. The mixture was acidified to pH 2 with aqueous HCl (1 M) and extracted with EtOAc (3×10 mL). The organic layers were combined and dried (MgSO4), filtered, concentrated in vacuo to give a cream white solid. The solid was triturated with cold CH2Cl2 to give 1-[2-(4-chlorophenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylic acid as a white solid (310 mg, 64%). 1H NMR (400 MHz, d6-DMSO): δ 5.86 (s, 2H), 6.16 (dd, 1H, J 3.9, 2.6 hz), 6.86 (dd, 1H, J 3.9, 1.8 Hz), 7.08 (t, 1H, J 2.1 Hz), 7.65-7.70 (m, 2H), 8.02-8.08 (m, 2H), 12.07 (br s, 1H).

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a cream white solid
  6. customThe solid was triturated with cold CH2Cl2

Sources & evidence

ORD record
ord-e7fd4182e347444ea3f5f25a2a69e2cd
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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