Iodine → 5-Iodo-7-nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline

HRID 494197Notes

Reaction equation

[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][N:11]2[C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[CH:6][CH:5]=1)([O-:3])=[O:2].II.[I:22]([O-])(=O)=O.[K+].O>S(=O)(=O)(O)O>[I:22][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][N:11]2[C:14](=[O:19])[C:15]([F:18])([F:16])[F:17]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 7-nitro-1-trifluoroacteyl-1,2,3,4-tetrahydroquinoline (D4) (2 g, 7.3 mmol) in conc. sulfuric acid (10 ml) was cooled to 0° C. and treated with iodine (1.11 μg, 4.4 mmol) and potassium iodate (0.625 g, 2.9 mmol). The reaction was stirred at 0° C. for 3 h then room temperature for 2 h. The reaction mixture was slowly poured into water (150 ml) at 0° C. and extracted with DCM. This was washed with aq. sodium metabisulfite and water then dried over MgSO4 and concentrated in vacuo to give the crude product. Purification by column chromatography gave the title compound (420 mg). 1H NMR (250 MHz, CDCl3) δ (ppm): 8.59 (m, 2H), 3.86 (m, 2H), 2.90 (t, 2H), 2.17 (m, 2H).

Workup

waitroom temperature for 2 h
extractionextracted with DCM
washThis was washed with aq. sodium metabisulfite and water
dry with materialthen dried over MgSO4
concentrationconcentrated in vacuo
customto give the crude product
customPurification by column chromatography

Sources & evidence

ORD record: ord-07b3bb6d5e234fd5981cc4fe45ab812e
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538121B2

Reaction notes

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