Pyridine → HCID 86738111, compound

HRID 1155370Notes

Reaction equation

HRID 1155370 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].O[C:9]1[CH:10]=[C:11]([C@@:15]23[CH2:24][C:23](=[O:25])[CH2:22][CH2:21][C@@H:20]2[CH2:19][N:18]([CH3:26])[CH2:17][CH2:16]3)[CH:12]=CC=1.N1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.O.C1(C)C=CC=CC=1>[C:5]([O:4][C:1]1[CH:12]=[C:11]([C@@:15]23[CH2:24][C:23](=[O:25])[CH2:22][CH2:21][C@@H:20]2[CH2:19][N:18]([CH3:26])[CH2:17][CH2:16]3)[CH:10]=[CH:9][CH:2]=1)(=[O:7])[CH3:6]

Participants

8

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 86738112HCID 86738112, compound

Product 1

HCID 86738111HCID 86738111, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

3.77 ml (40 mmol) of acetic anhydride are added dropwise to a stirred mixture of 5.19 g (20 mmol) of octahydro-4a-(3-hydroxyphenyl)-2-methyl-cis-6(2H)-isoquinoline (see Example 3), 3.22 ml (40 mmol) of pyridine and 20 ml of toluene at 5°. The mixture is then kept at 22° for 2 hours. 20 ml of water is added to the mixture at 5°, and the mixture is stirred for 30 minutes at 22°. 40 ml of methylene chloride are added. Whilst being stirred, the aqueous phase of the resultant twophase mixture is adjusted to pH 7 by the addition of 4 g of sodium carbonate. The aqueous phase is then separated and extracted with methylene chloride. The organic phases are washed with water, dried, concentrated by evaporation and dried in a high vacuum. The title compound is obtained as a viscous oil which is crystallized as the hydrogen fumarate from isopropanol; M.Pt. 194° (decomposition).

Workup

  1. stirringWhilst being stirred
  2. customThe aqueous phase is then separated
  3. extractionextracted with methylene chloride
  4. washThe organic phases are washed with water
  5. customdried
  6. concentrationconcentrated by evaporation
  7. customdried in a high vacuum

Sources & evidence

ORD record
ord-168ec4b035f043c08eceee2cf7224650
Source dataset
uspto-grants-1981_11
Patent number
US04301290

Reaction notes

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