Ethanol → HCID 57426223, compound

HRID 641436Notes

Reaction equation

HRID 641436 reaction equation
[CH:1]([C:4]1[NH:5][C:6]2[C:11]([C:12]=1[CH2:13][C:14]([OH:16])=[O:15])=[C:10]([N+:17]([O-:19])=[O:18])[CH:9]=[CH:8][CH:7]=2)([CH3:3])[CH3:2].OS(O)(=O)=O.[CH3:25][CH2:26]O>>[CH:1]([C:4]1[NH:5][C:6]2[C:11]([C:12]=1[CH2:13][C:14]([O:16][CH2:25][CH3:26])=[O:15])=[C:10]([N+:17]([O-:19])=[O:18])[CH:9]=[CH:8][CH:7]=2)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 57426222HCID 57426222, compound

Product 1

HCID 57426223HCID 57426223, compound

Procedure

A solution of (2-isopropyl-4-nitro-1H-indol-3-yl)acetic acid from Step D (500 mg, 1.91 mmol) and conc. H2SO4 (0.5 mL) in EtOH (100 mL) was heated at reflux for 1 h. The cooled mixture was partially concentrated in vacuo, made basic by addition of saturated aqueous NaHCO3 and washed with CHCl3 (4×30 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound, which was of sufficient purity for use in the next step. MS: m/z=291 (M+1).

Workup

  1. temperatureat reflux for 1 h
  2. concentrationThe cooled mixture was partially concentrated in vacuo
  3. additionmade basic by addition of saturated aqueous NaHCO3
  4. washwashed with CHCl3 (4×30 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8b93e5fd98894f09b0681e0e21ab271d
Source dataset
uspto-grants-2010_04
Patent number
US07696192B2

Reaction notes

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