Ethanol → HCID 14244939, compound

HRID 605389Notes

Reaction equation

HRID 605389 reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]1([C:15]([OH:17])=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7]1.[CH2:18](O)[CH3:19]>>[NH2:5][C:6]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7]1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 2338101-Amino-2,3-dihydro-1H-indene-1-carboxylic acid

Product 1

HCID 14244939HCID 14244939, compoundYield 84%

Procedure

Thionyl chloride (0.617 mL, 8.465 mmol) was added dropwise to anhydrous ethanol (6 mL) cooled to −30° followed by 1-amino-2,3-dihydro-1H-indene-1-carboxylic acid (0.300 g, 1.693 mmol) the reaction was then refluxed for 4 hours. The reaction was concentrated by rotary evaporation and diluted with water (5 mL) and the pH was adjusted to 9 with 6N aqueous sodium hydroxide. The solution was extracted with ethyl acetate (2×25 mL) and the organic extracts were washed with brine (25 mL), dried over sodium sulfate, filtered, and concentrated by rotary evaporation to afford the title compound as an oil (0.293 g, 1.43 mmol, 84%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.12 (t, J=7.17 Hz, 3 H) 1.85-2.07 (m, 1 H) 2.31 (s, 2 H) 2.51-2.66 (m, 1 H) 2.93 (t, J=6.99 Hz, 2 H) 3.90-4.21 (m, 2 H) 7.13-7.34 (m, 4 H). MS (DCI) m/z 206 (M+H)+, 223 (M+NH4)+.

Workup

  1. temperaturecooled to −30°
  2. temperaturewas then refluxed for 4 hours
  3. concentrationThe reaction was concentrated by rotary evaporation
  4. additiondiluted with water (5 mL)
  5. extractionThe solution was extracted with ethyl acetate (2×25 mL)
  6. washthe organic extracts were washed with brine (25 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-734c07ed12e44c7dabfbceee2bce657e
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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