Trifluoroacetic anhydride → 8-Hydroxy-5,6,7,8-tetrahydroquinoline-3-carbonitrile

HRID 1626134Notes

Reaction equation

HRID 1626134 reaction equation
[C:1]([C:3]1[CH:4]=[N+:5]([O-])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2].FC(F)(F)C(OC(=O)C(F)(F)F)=[O:17]>>[OH:17][CH:7]1[C:6]2[N:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:12][C:11]=2[CH2:10][CH2:9][CH2:8]1

Participants

3

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 682272013-Cyano-5,6,7,8-tetrahydroquinoline 1-oxide

Product 1

HCID 682271448-Hydroxy-5,6,7,8-tetrahydroquinoline-3-carbonitrileYield 87.2%

Conditions

Temperature
23 °C

Procedure

To a solution of 3-cyano-5,6,7,8-tetrahydroquinoline 1-oxide (645 mg, 3.7 mmol) was added dropwise under ice cooling trifluoroacetic anhydride (6.22 g, 4.18 ml, 29.6 mmol). The light yellow solution was stirred at 23° C. for 18 h. The mixture was quenched with a solution of sodium hydroxide (1N) and stirred vigorously for 30 minutes, then extracted twice with dichloromethane. The combined organic layers were dried over sodium sulphate, filtered and evaporated. The residue was purified by silica gel flash chromatography with n-heptane/ethyl acetate to give the 8-hydroxy-5,6,7,8-tetrahydroquinoline-3-carbonitrile (562 mg, 87% yield) as a white solid. MS (ISP): m/z=175.1 [M+H]+.

Workup

  1. customThe mixture was quenched with a solution of sodium hydroxide (1N)
  2. stirringstirred vigorously for 30 minutes
  3. extractionextracted twice with dichloromethane
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel flash chromatography with n-heptane/ethyl acetate

Sources & evidence

ORD record
ord-eae47f4663bc4a60a4da66e288f0ca2c
Source dataset
uspto-grants-2014_07
Patent number
US08785436B2

Reaction notes

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