Acetic Anhydride → HCID 18333093, compound

HRID 2269751Notes

Reaction equation

HRID 2269751 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([CH2:12][N:13]([CH3:15])[CH3:14])[CH2:8][NH:9]2)=[CH:4][CH:3]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>N1C=CC=CC=1.C1COCC1>[C:16]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([CH2:12][N:13]([CH3:15])[CH3:14])[CH2:8][NH:9]2)=[CH:4][CH:3]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 21940038HCID 21940038, compound

Product 1

HCID 18333093HCID 18333093, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-amino-3-(N,N-dimethylamino)methyl-1,2,3,4-tetrahydroquinoline (300 mg) in pyridine (3 ml) was added a solution of acetic anhydride (150 mg) in THF (1 ml) and stirring was continued for 30 minutes. The reaction mixture was purified by alumina column chromatography (eluent; ethyl acetate to ethyl acetate/methanol=20:1) and the resulting crystals were washed with IPE to obtain the entitled compound (275 mg).

Workup

  1. customThe reaction mixture was purified by alumina column chromatography (eluent; ethyl acetate to ethyl acetate/methanol=20:1)
  2. washthe resulting crystals were washed with IPE

Sources & evidence

ORD record
ord-9f58f1319a3e4cd8bb918c7426dbe360
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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