Sulfuric Acid → HCID 22720019, compound

HRID 1582230Notes

Reaction equation

HRID 1582230 reaction equation
C([O:5][C:6](=[O:28])[CH2:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:15]2[CH3:18])=[C:11]([C:24]([F:27])([F:26])[F:25])[CH:10]=1)(C)(C)C.S(=O)(=O)(O)O>C(O)(=O)C>[CH2:22]([O:21][C:19]([C:14]1[N:15]([CH3:18])[C:16]2[C:12]([CH:13]=1)=[C:11]([C:24]([F:25])([F:27])[F:26])[CH:10]=[C:9]([O:8][CH2:7][C:6]([OH:28])=[O:5])[CH:17]=2)=[O:20])[CH3:23]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 22720003HCID 22720003, compound

Product 1

HCID 22720019HCID 22720019, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Under nitrogen, ethyl 6-(2-tert-butoxy-2-oxoethoxy)-1-methyl-4-(trifluoromethyl)-1H-indole-2-carboxylate (1.3 g, 3.24 mmol) was dissolved in acetic acid (20 ml), followed by adding thereto a 30% aqueous sulfuric acid solution (10 ml), and the resulting mixture was stirred at 50° C. for 1 hour. Crystals were precipitated and the reaction mixture became a white suspension. The reaction mixture was cooled to room temperature, followed by adding thereto water, and the crystals precipitated were collected by filtration, washed with water, and then dried under reduced pressure to obtain 1.17 g of [[2-(ethoxycarbonyl)-1-methyl-4-(trifluoromethyl)-1H-indol-6-yl]oxy]acetic acid as white crystals.

Workup

  1. additionby adding
  2. customCrystals were precipitated
  3. additionby adding
  4. customwater, and the crystals precipitated
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-49298f5b1b2c4a579e25a5d5bf7744f6
Source dataset
uspto-grants-2004_05
Patent number
US06734205B2

Reaction notes

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