Hydrochloric Acid → HCID 22221627, compound

HRID 1835984Notes

Reaction equation

HRID 1835984 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:20]([OH:22])=[O:21])[C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:19]=1.Cl.N1C=CC=CC=1.Cl>>[OH:2][C:3]1[CH:4]=[C:5]([C:20]([OH:22])=[O:21])[C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:19]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chlorideHCID 10308394HCID 10308394, compound

Product 1

HCID 22221627HCID 22221627, compoundYield 77%

Conditions

Temperature
200 °C

Procedure

To acid 23 (0.075 g, 0.250 mmole) was added pyridine-HCl (5.1 g, 43.3 mmole). After stirring at 200° C. for 30 minutes, the mixture was cooled to rt, poured into 2N HCl aq. and extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate, water, brine, and dried with magnesium sulfate. The organic phases were concentrated and the residue was loaded on to silica gel and chromatographed with silica gel (hexanes:ethyl acetate, 1:1) to afford 0.052 g (77%) of acid 24 as a white solid: Mp=260-262° C.; 1H NMR (DMSO-d6) δ 13.3 (br s,1 H), 9.79 (br s, 1 H), 9.46 (br s,1 H), 7.91 (d, 2 H, J=8.7 Hz), 7.30 (d, 1 H, J=2.4 Hz), 7.11 (s, 1 H), 7.08 (d, 1 H, J=2.4 Hz), 6.98 (d, 2 H, J=8.9 Hz); MS 269 (M−H)− Product was still contaminated with some 3-Cl compound.

Workup

  1. temperaturethe mixture was cooled to rt
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases were washed with saturated sodium bicarbonate, water, brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationThe organic phases were concentrated
  6. customchromatographed with silica gel (hexanes:ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-825d0914a2da4be19c2ad2399589b588
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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