Formic Acid → HCID 11148287, compound

HRID 419929Notes

Reaction equation

HRID 419929 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH:9][CH2:10][CH2:11][OH:12].Cl.[OH-].[Na+].[CH:16](O)=O>>[Cl:1][C:2]1[C:3]2[N:9]([CH2:10][CH2:11][OH:12])[CH:16]=[N:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11159758HCID 11159758, compound

Product 1

HCID 11148287HCID 11148287, compoundYield 93%

Procedure

The 2-[(2-chloro-6-aminophenyl)amino]ethanol (72.4 g, 0.388 mol), is dissolved in formic acid (350 ml) and stirred under reflux for 1 hour. The reaction mixture is concentrated to dryness under reduced pressure to give a dark solid, then 500 ml of HCl 2N is added to the residue and the mixture is heated under reflux for 30 min. The solution is cooled on ice and 50% NaOH solution is added until alkaline and the obtained suspension is filtered under vacuum and the resulting solid dried to give the desired product (70.8 g 93%)

Workup

  1. temperatureunder reflux for 1 hour
  2. concentrationThe reaction mixture is concentrated to dryness under reduced pressure
  3. customto give a dark solid
  4. temperaturethe mixture is heated
  5. temperatureunder reflux for 30 min
  6. additionis added until alkaline
  7. filtrationthe obtained suspension is filtered under vacuum
  8. customthe resulting solid dried

Sources & evidence

ORD record
ord-a8dac802e8d740a4a883639e992e4c5b
Source dataset
uspto-grants-2012_01
Patent number
US08093402B2

Reaction notes

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