Propionyl chloride → HCID 22033703, compound

HRID 1791882Notes

Reaction equation

HRID 1791882 reaction equation
[CH2:1]([C:8]1[CH:17]=[C:12]([C:13]([O:15]C)=[O:14])[C:11]([NH2:18])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19](Cl)(=[O:22])[CH2:20][CH3:21].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:18][C:19](=[O:22])[CH2:20][CH3:21])=[C:12]([CH:17]=1)[C:13]([OH:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 516892Sodium BicarbonateHCID 22033706HCID 22033706, compound

Product 1

HCID 22033703HCID 22033703, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 5-benzylanthranilate (300 mg; 1.24 mmols) was dissolved in 7 mL of chloroform and propionyl chloride (344 mg; 3.72 mmols) was added and the reaction mixture was left at room temperature for 18 hours. Aqueous saturated sodium bicarbonate (5 mL) was added to the reaction mixture whereafter the organic phase was separated, dried over magnesium sulphate, filtered and evaporated to dryness. The resulting yellow oil was dissolved in 5 mL of methanol and aqueous sodium hydroxide (1M, 5 mL) was added. The reaction mixture was then heated to 60° C. for two hours. After cooling to room-temperature the reaction mixture was acidified with 20 mL of hydrochloric acid (1M). The white precipitate was filtered with suction, washed twice with water and dried under vacuum yielding the title compound quantitatively. 1H NMR (DMSO-d6) δ 1.09 (t, 3H, J=7.4, —CH3), 2.37 (q, 2H, J=7.5, —CH2—CH3), 3.92 (s, 2H, —CH2-Ph), 7.13–7.45 (m, 5H, -Ph), 7.44 (d, 1H, J=8.6, H4), 7.79 (s, 1H, H6), 8.39 (d, 1H, J=8.5, H3), 11.01 (s, 1H, >NH), 13.54 (bs, 1H, —COOH).

Workup

  1. customwas separated
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. dissolutionThe resulting yellow oil was dissolved in 5 mL of methanol
  6. additionaqueous sodium hydroxide (1M, 5 mL) was added
  7. temperatureAfter cooling to room-temperature the reaction mixture
  8. filtrationThe white precipitate was filtered with suction
  9. washwashed twice with water
  10. customdried under vacuum

Sources & evidence

ORD record
ord-3ad511abece24f04a183842d292cd7fa
Source dataset
uspto-grants-2006_07
Patent number
US07074831B2

Reaction notes

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