Hydrochloric Acid → HCID 53234444, compound

HRID 239612Notes

Reaction equation

HRID 239612 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:17])=[C:6]([C:8](=[O:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=1.[C:18](OC(=O)CC)(=O)[CH2:19][CH3:20].Cl>C(N(CC)CC)C>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:17][C:18]([CH2:19][CH3:20])=[C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:8]2=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31263Propionic anhydrideHCID 12209494HCID 12209494, compound

Product 1

HCID 53234444HCID 53234444, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Intermediate 1 (2.0 g, 6.86 mmoles) was taken in a RB flask and to this triethylamine (16 ml) and propionic anhydride (2.80 g, 21.50 mmoles) were added and the mixture was refluxed for 22 h. After cooling to RT, the reaction mixture was acidified by the addition of 1N HCl solution, extracted with ethyl acetate, washed with sodium bicarbonate solution, dried with sodium sulphate and concentrated. The crude product was purified by column chromatography with ethyl acetate : petroleum ether to afford the title compound as off-white solid (0.78 g, 31% yield). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 8.10(d, J=2.4 Hz, 1H), 7.97(dd, J=8.9,2.4 Hz, 1H), 7.68(d, J=8.9 Hz, 1H), 7.46(m, 3H),7.27(d, J=6.9 Hz, 2H), 2.55(q, J=7.5 Hz, 2H), 1.19(t, J=7.5 Hz, 3H).

Workup

  1. additionwere added
  2. temperaturethe mixture was refluxed for 22 h
  3. extractionextracted with ethyl acetate
  4. washwashed with sodium bicarbonate solution
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography with ethyl acetate

Sources & evidence

ORD record
ord-0a431c326bea4790bfd9e3dad8eddd09
Source dataset
uspto-grants-2014_02
Patent number
US08642607B2

Reaction notes

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