Acetic Acid → 1-(4-aminosulfonylphenyl)methylene-5-methoxy-2-methyl-1H-3-indenyl acetic acid

HRID 542225Notes

Reaction equation

HRID 542225 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7]([CH3:12])=[C:6]2[CH2:13][C:14]([OH:16])=[O:15].[OH-].[K+].[NH2:19][S:20]([C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1)(=[O:22])=[O:21].C(O)(=O)C>CO>[NH2:19][S:20]([C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[C:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[C:6]([CH2:13][C:14]([OH:16])=[O:15])=[C:7]2[CH3:12])=[CH:25][CH:24]=1)(=[O:21])=[O:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 1510884-SulfamoylbenzaldehydeHCID 139332542-(5-methoxy-2-methyl-1H-inden-3-yl)acetic acid

Product 1

HCID 676380441-(4-aminosulfonylphenyl)methylene-5-methoxy-2-methyl-1H-3-indenyl acetic acidYield 57.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 5-methoxy-2-methyl-3-indenylacetic acid (1a) (3.95 g) in 90% methanol (24 ml) containing 85% potassium hydroxide (2.7 g) was added a solution of p-aminosulfonylbenzaldehyde (3.70 g) in 90% methanol (24 ml). The resulting mixture was refluxed under nitrogen for 4-6 hours. A solution of 50% aqueous acetic acid (50 ml) was then added to the reaction mixture during 40 minutes at 50°-60° C. The crystals were collected after aging at 15° C. for 1 hour. The crude product was recrystallized five times from acetone-hexane to give pure Z form of 1-(4-aminosulfonylphenyl)methylene-5-methoxy-2-methyl-1H-3-indenylacetic acid (2a) (4.0 g, 57%): m.p. 224°-225° C.; Rf =0.45 (silica gel, 10% MeOH in CHCl3 developed 3-4 times).

Workup

  1. temperatureThe resulting mixture was refluxed under nitrogen for 4-6 hours
  2. customThe crystals were collected
  3. customThe crude product was recrystallized five times from acetone-hexane

Sources & evidence

ORD record
ord-eba66881959b4d7980cc16a1f8c5aa40
Source dataset
uspto-grants-1987_04
Patent number
US04656190

Reaction notes

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