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

HRID 1490370Notes

Reaction equation

HRID 1490370 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-1987e16e302040f5b5cf01e814223d2b
Source dataset
uspto-grants-1997_10
Patent number
US05681961

Reaction notes

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