Hydrochloric Acid → Methyl 6-(2-aminoindan-5-yl)-6-(3-pyridyl)hex-5-enoate

HRID 22112Notes

Reaction equation

HRID 22112 reaction equation
C([NH:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:14]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[CH:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:11]=2)[CH2:6]1)(=O)C.Cl.[CH3:29]O>>[NH2:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:14]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[CH:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:29])=[O:20])[CH:11]=2)[CH2:6]1

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 541041176-(2-Acetylaminoindan-5-yl)-6-(3-pyridyl)hex-5-enoic acid

Product 1

HCID 54311386Methyl 6-(2-aminoindan-5-yl)-6-(3-pyridyl)hex-5-enoate

Procedure

3.1 g of 6-(2-acetylaminoindan-5-yl)-6-(3-pyridyl)hex-5-enoic acid are refluxed for 15 hours with 20 ml of half concentrated hydrochloric acid and then rotary evaporated. The residue is then added to 50 ml of methanol saturated with dry hydrogen chloride. After 30 minutes stirring at ambient temperature the reaction mixture is rotary evaporated to dryness. The residue is taken up in 1N sodium hydroxide solution and adjusted to pH 10. It is then extracted 3 times with 50 ml of methylene chloride, the organic phase is dried and rotary evaporated.

Workup

  1. customis rotary evaporated to dryness
  2. extractionIt is then extracted 3 times with 50 ml of methylene chloride
  3. customthe organic phase is dried

Sources & evidence

ORD record
ord-5f521627dad447fd88ae21161734a681
Source dataset
uspto-grants-1995_06
Patent number
US05426119

Reaction notes

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