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

HRID 403250Notes

Reaction equation

HRID 403250 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 87.3%

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 1 N NaOH solution and stirred vigorously for 30 min., then extracted twice with dichloromethane, the combined organic layers were dried over Na2SO4, 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, 3.23 mmol, 87.1% yield) as a white solid. MS (ISP): m/z=175.1 [(M+H)+].

Workup

  1. customThe mixture was quenched with 1 N NaOH solution
  2. stirringstirred vigorously for 30 min.
  3. extractionextracted twice with dichloromethane
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel flash chromatography with n-heptane/ethyl acetate

Sources & evidence

ORD record
ord-42265fac923e4eac80892ee86323924e
Source dataset
uspto-grants-2014_06
Patent number
US08748418B2

Reaction notes

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