Acetic Acid → HCID 19592540, compound

HRID 613570Notes

Reaction equation

HRID 613570 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]([CH3:22])[CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[NH:17][N:18]=[C:19]([CH3:21])[CH3:20])=[O:5].C([BH3-])#N.[Na+].C(O)(=O)C>CO>[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]([CH3:22])[CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[NH:17][NH:18][CH:19]([CH3:20])[CH3:21])=[O:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 19592796HCID 19592796, compound

Product 1

HCID 19592540HCID 19592540, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 8-(2,6-dichlorobenzoylamino)-6-methyl-4-(2-isopropylidenehydrazino)quinoline (159 mg) in methanol (5 ml) was added sodium cyanoborohydride (25 mg) and acetic acid (50 mg), and the mixture was stirred at ambient temperature for 24 hours. The mixture was concentrated to dryness and the residue was triturated with water (5 ml) and filtered. The solid was treated with hot water (5 ml), allowed to cool to ambient temperature, filtered and washed with water to give 8-(2,6-dichlorobenzoylamino)-6-methyl-4-(2-isopropylhydrazino)quinoline (117 mg) as pale yellow powder.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. customthe residue was triturated with water (5 ml)
  3. filtrationfiltered
  4. additionThe solid was treated with hot water (5 ml)
  5. temperatureto cool to ambient temperature
  6. filtrationfiltered
  7. washwashed with water

Sources & evidence

ORD record
ord-c95faae39b564ed4b99cc60a79f7691a
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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