Acetic Acid → HCID 46945577, compound

HRID 1470584Notes

Reaction equation

HRID 1470584 reaction equation
[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(O)(=O)C.[F:16][C:17]1[CH:18]=[C:19]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=2)[CH:20]=[CH:21][C:22]=1[CH:23]=O.[S-2].[Na+].[Na+]>CO.O.Cl>[F:16][C:17]1[CH:18]=[C:19]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=2)[CH:20]=[CH:21][C:22]=1[C:23]1[NH:11][C:10]2[CH:9]=[CH:8][CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]=2[N:1]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 14804Sodium SulfideHCID 1980692,3-Diaminobenzoic acidHCID 23005037HCID 23005037, compound

Product 1

HCID 46945577HCID 46945577, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of 2,3-diaminobenzoic acid (0.15 g, 0.824 mmol) in methanol (2 mL) was acidified with acetic acid (0.5 mL) To this mixture was added a solution of 3-fluoro-3′-methoxy-biphenyl-4-carbaldehyde (0.2466 g, 1.0695 mmol) in methanol followed by a solution of cupric acetate (0.183 g, 0.919 mmol) in water (4 mL). The resulting mixture was stirred vigorously and heated to 70° C. for 5 minutes and then filtered hot. The precipitate was washed with water and dissolved in ethanol (5 mL) containing 0.5 mL conc. HCl. A solution of sodium sulphide (0.082 g, 1.0512 mmol) in water was added. The reaction mixture was kept acidic by adding 2-3 drops of conc HCl. The reaction mixture was filtered hot to remove copper sulfide. The pH of the solution adjusted to 4 and diluted with water. The precipitate formed was filtered, washed with water and dried. The residue obtained was purified by column chromatography using 5% methanol in dichloromethane to obtain the title compound.

Workup

  1. filtrationfiltered hot
  2. washThe precipitate was washed with water
  3. dissolutiondissolved in ethanol (5 mL)
  4. additioncontaining 0.5 mL conc. HCl
  5. filtrationThe reaction mixture was filtered hot
  6. customto remove copper sulfide
  7. additiondiluted with water
  8. customThe precipitate formed
  9. filtrationwas filtered
  10. washwashed with water
  11. customdried
  12. customThe residue obtained
  13. customwas purified by column chromatography

Sources & evidence

ORD record
ord-795b15bf29c146638ac5fc903bc94985
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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