Formic Acid → HCID 178525382, compound

HRID 2289987Notes

Reaction equation

HRID 2289987 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([C:21]#[C:22][CH2:23][OH:24])=[CH:15][C:14]=3[F:25])=[O:9])=[CH:4][CH:3]=1.[CH:28](O)=[O:29]>>[CH:28]([O:24][CH2:23][C:22]#[C:21][C:16]1[CH:17]=[C:18]2[C:13](=[C:14]([F:25])[CH:15]=1)[N:12]=[CH:11][C:10]([C:8]([NH:7][CH2:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:27][CH:26]=1)=[O:9])=[C:19]2[OH:20])=[O:29]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 178522909HCID 178522909, compound

Product 1

HCID 178525382HCID 178525382, compoundYield 44%

Procedure

A solution of N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide from Example No. 53 (0.15 g) in 6 mL formic acid is heated at 100° C. for 6 hours. Once the reaction is cooled to room temperature, it is partitioned between CH2Cl2 and water. The organic layer is washed with water, saturated NaHCO3, and water again. The organic layer is dried over MgSO4, filtered and concentrated under reduced pressure to give a residue which is crystallized with CH2Cl2 /hexanes to give the product (0.070 g, 44%).

Workup

  1. customit is partitioned between CH2Cl2 and water
  2. washThe organic layer is washed with water, saturated NaHCO3, and water again
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a residue which
  7. customis crystallized with CH2Cl2 /hexanes

Sources & evidence

ORD record
ord-2a4e27488a494eaea721c52152ead4e3
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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