Hydrochloric Acid → HCID 59615663, compound

HRID 384417Notes

Reaction equation

HRID 384417 reaction equation
C[O:2][C:3]([C:5]1[N:6](S(C2C=CC(C)=CC=2)(=O)=O)[CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[C:11]=2[O:19][CH3:20])[CH:9]=1)=[O:4].O.[OH-].[Li+].CN(C)C=O.Cl>O>[N+:16]([C:12]1[C:11]([O:19][CH3:20])=[C:10]([C:8]2[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[NH:6][CH:7]=2)[CH:15]=[CH:14][CH:13]=1)([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 168937Lithium hydroxide, monohydrateHCID 596156904-(3-nitro-2-methoxy-phenyl)-1-(p-tolylsulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester

Product 1

HCID 59615663HCID 59615663, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(3-Nitro-2-methoxy-phenyl)-1-(p-tolylsulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester 57f (1.04 g, 2.42 mmol) and lithium hydroxide monohydrate (1.01 g, 24.19 mmol) were added to a solvent mixture of 10 mL of N,N-dimethylformamide and 5 mL of water. The reaction mixture was reacted at 100° C. for 30 minutes under microwave. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was adjusted to pH 3 with hydrochloric acid (1 N) to form a lot of precipitates. The mixture was filtered and the filter cake was dried to obtain the title compound 4-(3-nitro-2-methoxy-phenyl)-1H-pyrrole-2-carboxylic acid 57g (350 mg, yield 50%) as a yellow solid.

Workup

  1. customThe reaction mixture was reacted at 100° C. for 30 minutes under microwave
  2. customto form a lot
  3. customof precipitates
  4. filtrationThe mixture was filtered
  5. customthe filter cake was dried

Sources & evidence

ORD record
ord-353618725e4349b891b7eaa36d566d79
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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