Water → 1-Acetyl-7-chloro-beta-carboline

HRID 1795085Notes

Reaction equation

HRID 1795085 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:11]=3[NH:12]2)=[CH:4][CH:3]=1.[H-].[Na+].[C:17](OC(=O)C)(=[O:19])[CH3:18].O>CN(C=O)C>[C:17]([C:10]1[C:11]2[NH:12][C:13]3[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:14]=3)[C:6]=2[CH:7]=[CH:8][N:9]=1)(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 221852817-Chloro-beta-carboline

Product 1

HCID 221852721-Acetyl-7-chloro-beta-carboline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product from example 12 (104 mg, 0.50 mmol) in DMF (2.0 ml) at 3° C. to 5° C. was added NaH (95%, 15 mg, 0.625 mmol). The resulting mixture was stirred for 15 min before adding acetic anhydride (0.083 ml, 0.875 mmol). The reaction was allowed to warm to RT and stirred for 3 h before pouring into with water (25 ml). The slurry was stirred for 12 h, and the product collected to give after chromatography (1:3 hexane-ethyl acetate) on silica gel 82 mg of 1-acetyl-7-chloro-β-carboline.

Workup

  1. stirringstirred for 3 h
  2. stirringThe slurry was stirred for 12 h
  3. customthe product collected

Sources & evidence

ORD record
ord-13826f7f975c4c04b437a51297a8b9ac
Source dataset
uspto-grants-2006_04
Patent number
US07026331B2

Reaction notes

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