Toluene → HCID 59198430, compound

HRID 1971012Notes

Reaction equation

HRID 1971012 reaction equation
[OH:1][C:2]1[CH:7]=[C:6](O)[CH:5]=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16]N)=[CH:12][CH:11]=1.C(O)(C)C.C1(C)C=CC=CC=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[F:9][C:10]1[CH:15]=[CH:14][C:13]2[NH:16][C:6]3[CH:5]=[CH:4][NH:3][C:2](=[O:1])[C:7]=3[C:12]=2[CH:11]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 3776IsopropanolHCID 69982(4-Fluorophenyl)hydrazineHCID 178516518HCID 178516518, compound

Product 1

HCID 59198430HCID 59198430, compound

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent2×

Conditions

Temperature
165 °C

Procedure

To 2,4-dihydroxypyridine (43.6 g, 392 mmol) in phenyl ether (760 mL) in a three neck flask fitted with a Dean-Stark trap was added 4-fluorophenylhydrazine in phenyl ether (100 mL). The reaction mixture was heated to 165° C. for 1 h, slowly warmed to 230° C., and left to stir at 230° C. for 1 h. The reaction mixture was allowed to cool to 45° C. and treated with isopropanol and toluene. The mixture was filtered, washed with toluene, and dried to give the title compound. 1H NMR (600 MHz, CD3SOCD3) δ 11.82 (s, 1H); 11.13 (s, 1H); 7.71 (dd, 1H); 7.45 (dd, 1H); 7.28 (t, 1H); 7.12 (m, 1H); 6.45 (d, 1H). LRMS (APCI) calc'd for (C11H7FN2O) [M+H]+, 203.1. found 203.1.

Workup

  1. temperatureslowly warmed to 230° C.
  2. waitleft
  3. temperatureto cool to 45° C.
  4. filtrationThe mixture was filtered
  5. washwashed with toluene
  6. customdried

Sources & evidence

ORD record
ord-e0863f3a2b0240bb83569c480489a8de
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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