Acetone → 2-(2,3-Dimethyl-4-(2-methyl-4-nitro-1H-indol-5-yloxy)phenyl)acetic acid

HRID 2423288Notes

Reaction equation

HRID 2423288 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[C:9]([CH3:17])[C:8]=2[CH3:18])=[C:4]([N+:21]([O-:23])=[O:22])[CH:3]=1.[CH3:24][C:25]([CH3:27])=O.CC(C)([O-])C.[K+]>CS(C)=O.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH3:17][C:9]1[C:8]([CH3:18])=[C:7]([O:6][C:5]2[C:4]([N+:21]([O-:23])=[O:22])=[C:3]3[C:2](=[CH:20][CH:19]=2)[NH:1][C:25]([CH3:27])=[CH:24]3)[CH:12]=[CH:11][C:10]=1[CH2:13][C:14]([OH:16])=[O:15]

Participants

7

Reactant 3

HCID 180AcetoneHCID 23665647Potassium tert-butoxideHCID 598648252-(4-(4-Amino-2-nitrophenoxy)-2,3-dimethylphenyl)acetic acid

Product 1

HCID 598648942-(2,3-Dimethyl-4-(2-methyl-4-nitro-1H-indol-5-yloxy)phenyl)acetic acid

Reagents, catalysts & solvents 3

HCID 311Citric AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Under an N2 atmosphere, 2-(4-(4-amino-2-nitrophenoxy)-2,3-dimethylphenyl)acetic acid (0.723 g, 2.29 mmol) was dissolved in DMSO (18 mL) and acetone (0.503 mL, 6.86 mmol) was added. The reaction was treated with potassium tert-butoxide (0.770 g, 6.86 mmol) and allowed to stir at room temperature for 1.5 h. The reaction was diluted with water and citric acid was added to pH 4. The mixture was extracted with ethyl acetate. The aqueous layer was washed with additional ethyl acetate. The organics were combined, dried (Na2SO4), filtered and concentrated in vacuo. Flash column chromatography of the residue, eluting with 0% to 9% methanol in dichloromethane, afforded the title compound. LC-MS ESI (neg.) m/z: 353.2 (M−H).

Workup

  1. additionwas added to pH 4
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe aqueous layer was washed with additional ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washFlash column chromatography of the residue, eluting with 0% to 9% methanol in dichloromethane

Sources & evidence

ORD record
ord-536bbeed8fda4a5985f59be436375e90
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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