Hydrochloric Acid → HCID 12799987, compound

HRID 2412635Notes

Reaction equation

HRID 2412635 reaction equation
Cl.[CH2:2]([CH:10]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([OH:21])=[O:20])=[CH:16][CH:17]=2)[NH:12][CH2:11]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].Cl.[CH3:23]O>>[CH2:2]([CH:10]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([O:21][CH3:23])=[O:20])=[CH:16][CH:17]=2)[NH:12][CH2:11]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 24839534HCID 24839534, compound

Product 1

HCID 12799987HCID 12799987, compound

Procedure

(RS)-3-(n-Octyl)indoline-6-carboxylic acid hydrochloride (7.5 g) in methanol (500 ml), containing hydrochloric acid (50 ml, of strength 36% w/v), was refluxed for 18 hours. The solvent was removed in vacuo and water (100 ml) was added to the residue to give a solid, which was collected, washed with water (2×200 ml) and dried. The solid was dissolved in dichloromethane and was washed with an aqueous solution of sodium bicarbonate (100 ml of strength 2% w/v) and then water (100 ml) and was dried over sodium sulphate. The solvent was removed in vacuo to give a pale yellow oil, which solidified. The solid was recrystallised from a mixture (4:1) of methanol and water to give (RS)-methyl 3-(n-octyl)indoline-6-carboxylate (4.8 g), in the form of a white solid, m.p. 57°-60° C.

Workup

  1. temperaturewas refluxed for 18 hours
  2. customThe solvent was removed in vacuo and water (100 ml)
  3. additionwas added to the residue
  4. customto give a solid, which
  5. customwas collected
  6. washwashed with water (2×200 ml)
  7. customdried
  8. dissolutionThe solid was dissolved in dichloromethane
  9. washwas washed with an aqueous solution of sodium bicarbonate (100 ml of strength 2% w/v)
  10. dry with materialwater (100 ml) and was dried over sodium sulphate
  11. customThe solvent was removed in vacuo
  12. customto give a pale yellow oil, which
  13. customThe solid was recrystallised from a mixture (4:1) of methanol and water

Sources & evidence

ORD record
ord-7d1e7d9d7a4f48be89b6d91061fb1439
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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