Hydrochloric Acid → HCID 178467390, compound

HRID 1982607Notes

Reaction equation

HRID 1982607 reaction equation
[CH2:1]([CH:3]1[C:7]2=[N:8][C:9]3[C:10]([F:17])=[CH:11][CH:12]=[CH:13][C:14]=3[C:15]([OH:16])=[C:6]2[C:5](=[N:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)[O:4]1)C.Cl.[OH2:25]>>[F:17][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[C:7]([CH:3]([OH:25])[CH3:1])[C:6]([C:5]([NH:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1)=[O:4])=[C:15]2[OH:16]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178438187HCID 178438187, compound

Product 1

HCID 178467390HCID 178467390, compound

Conditions

Temperature
50 °C

Procedure

A mixture of 5 g of the product of Step F and 50 ml of 6N hydrochloric acid was heated at 50° C. for 5 hours and after addition of 50 ml of water, the mixture was cooled to 0° to 5° C. for 30 minutes and was vacuum filtered. The product was washed with water and dried under reduced pressure at 80° C. The product was successively chromatographed over silica gel twice and eluted with a 9-1 chloroform-methanol mixture to obtain 1.15 g of 8-fluoro-4-hydroxy-2-(1-hydroxyethyl)-N-(2-thiazolyl)-3-quinoline-carboxamide.

Workup

  1. temperaturethe mixture was cooled to 0° to 5° C. for 30 minutes
  2. filtrationfiltered
  3. washThe product was washed with water
  4. customdried under reduced pressure at 80° C
  5. customThe product was successively chromatographed over silica gel twice
  6. washeluted with a 9-1 chloroform-methanol mixture

Sources & evidence

ORD record
ord-bcdb2bd3832845dfb850a24189f27233
Source dataset
uspto-grants-1986_06
Patent number
US04596875

Reaction notes

Loading…