Acetic Anhydride → HCID 54325627, compound

HRID 2290925Notes

Reaction equation

HRID 2290925 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:16]2[CH2:15][CH2:14][C@H:13]3[C@@H:9]([CH2:10][NH:11][CH2:12]3)[C:8]=2[CH:7]=[CH:6][C:5]=1[O:17][CH3:18].[C:19](OC(=O)C)(=[O:21])[CH3:20]>N1C=CC=CC=1>[C:19]([N:11]1[CH2:10][C@@H:9]2[C@H:13]([CH2:14][CH2:15][C:16]3[C:4]([O:3][CH3:2])=[C:5]([O:17][CH3:18])[CH:6]=[CH:7][C:8]=32)[CH2:12]1)(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 70453900HCID 70453900, compound

Product 1

HCID 54325627HCID 54325627, compoundYield 114.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of trans-2,3,3a,4,5,9b-hexahydro-6,7-dimethoxy-1H-benz[e]isoindole hydrochloride (0.50 g, 1.9 mmole) and dry pyridine (9.5 mL) was stirred under N2 at room temperature as acetic anhydride (0.26 mL, 2.8 mmole) was added dropwise. The reaction mixture was stirred at room temperature for 0.75 hr, then was evaporated (in-vacuo). 2-Methoxyethanol was added and evaporated. The residue was dissolved in CH2Cl2 and was washed with 1N HCl, 1N KOH, water, saturated aqueous NaCl, dried (MgSO4), filtered and evaporated to yield 0.60 g white solid; M+ 275.

Workup

  1. additionwas added dropwise
  2. customwas evaporated (in-vacuo)
  3. addition2-Methoxyethanol was added
  4. customevaporated
  5. dissolutionThe residue was dissolved in CH2Cl2
  6. washwas washed with 1N HCl, 1N KOH, water, saturated aqueous NaCl
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-27c9f7ae82674980a71c3c6b0bfe8b1c
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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