Acetic Anhydride → HCID 18328986, compound

HRID 1034256Notes

Reaction equation

HRID 1034256 reaction equation
[CH3:1][CH:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][C:9]([O:15][CH3:16])=[CH:10][CH:11]=3)[C:6]=2[CH2:5][CH2:4][NH:3]1.[C:17](OC(=O)C)(=[O:19])[CH3:18]>[NH4+].[OH-].C(OCC)(=O)C>[CH3:1][CH:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][C:9]([O:15][CH3:16])=[CH:10][CH:11]=3)[C:6]=2[CH2:5][CH2:4][N:3]1[C:17](=[O:19])[CH3:18]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 710282,3,4,9-Tetrahydro-6-methoxy-1-methyl-1H-pyrido(3,4-b)indole

Product 1

HCID 18328986HCID 18328986, compound

Reagents, catalysts & solvents 2

HCID 14923Ammonium HydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 700 mg (3.24 mmol) 1-methyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline, and 5 drops NH4OH in ethyl acetate was added 0.4 mL (3.88 mmol) acetic anhydride under N2 gas. The reaction was stirred for 20 min. and then washed with water. The organic layer collected was dried over MgSO4, filtered, and concentrated in vacuo to a dark oil. The oil was dissolved in methanol and chromatographed on reverse phase C-18 using methanol and water. The product was collected and concentrated to a white solid, which showed characteristic peaks: NMR (CDCl3) δ: 1.45 ppm (d, 3H), 2.25 ppm (s, 3H), 3.85 ppm (s, 3H).

Workup

  1. washwashed with water
  2. customThe organic layer collected
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a dark oil
  6. dissolutionThe oil was dissolved in methanol
  7. customchromatographed on reverse phase C-18
  8. customThe product was collected
  9. concentrationconcentrated to a white solid, which

Sources & evidence

ORD record
ord-36e5f3b52127447b84cfc08d4bcd774f
Source dataset
uspto-grants-1994_05
Patent number
US05314908

Reaction notes

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