Acetic Anhydride → 8-Acetoxy-6-benzyloxycarbonylamino-5,6,7,8-tetrahydroquinoline

HRID 1765329Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:21][CH2:20][C:19]2[N+:18]([O-])=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O:26]C(=O)C)(=[O:25])[CH3:24]>C(Cl)Cl>[C:23]([O:26][CH:20]1[C:19]2[N:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:13][CH:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:21]1)(=[O:25])[CH3:24]

Participants

Conditions

Temperature: 60 °C

Procedure

6-Benzyloxycarbonylamino-5,6,7,8-tetrahydroquinoline 1-oxide (1.62 g, 5.44 mmol) was dissolved in acetic anhydride (7.7 mL, 81.6 mmol), and the reaction mixture was stirred at 60° C. for 2 h under nitrogen. After this time, the solvent was removed under vacuum to yield a residue, which was dissolved in methylene chloride. The resulting solution was washed sequentially with water, saturated aqueous sodium carbonate solution and brine, dried over anhydrous magnesium sulfate, and evaporated under vacuum to obtain the title compound (1.73 g, 93%) as a brown oil. HPLC/MS [M+H]+, 341.

Workup

customAfter this time, the solvent was removed under vacuum
customto yield a residue, which
washThe resulting solution was washed sequentially with water, saturated aqueous sodium carbonate solution and brine
dry with materialdried over anhydrous magnesium sulfate
customevaporated under vacuum

Sources & evidence

ORD record: ord-c638e07253b1432a849c8ca7b7725b67
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07226942B2

Reaction notes

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