Hydrochloric Acid → HCID 22221627, compound

HRID 1794481Notes

Reaction equation

HRID 1794481 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 magnesiumsulfate. 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 magnesiumsulfate
  5. concentrationThe organic phases were concentrated
  6. customchromatographed with silica gel (hexanes:ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-95cda85969dd44aa823a97f831ebd1ae
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

Loading…