Acetic Acid → HCID 16128890, compound

HRID 1822099Notes

Reaction equation

HRID 1822099 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][C:3]=1[C:12](=[O:15])[CH2:13][Cl:14].[BH4-].[Na+].C(O)(=O)C>C(O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][C:3]=1[CH:12]([OH:15])[CH2:13][Cl:14]

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 37309465-chloroacetyl-6-chlorooxindoleHCID 4311764Sodium borohydride

Product 1

HCID 16128890HCID 16128890, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A reactor is loaded with 200 g (0.82 mol) of 6-chloro-5-(2-chloro-acetyl)-1,3-dihydro-indol-2-one, in 1 L of ethanol. The reaction mixture is added with 15.5 g (0.41 mol) of sodium borohydride in portions, under strong stirring, at room temperature. The temperature is kept at 15-20° C. during the addition, after that the mixture is left under stirring for about 15 h at room temperature. The mixture is then added with 250 ml of glacial acetic acid and refluxed (approx. 85° C.) for 1 hr 30 min, then 200 ml of acetic acid are added and the mixture is refluxed a further 30 min, then cooled to 20° C. The suspension is filtered and washed with ethanol and heptane. The solid product is dried under vacuum at a temperature of 60° C., to obtain 177 g (88% molar yield).

Workup

  1. additionThe temperature is kept at 15-20° C. during the addition
  2. waitafter that the mixture is left
  3. temperaturerefluxed (approx. 85° C.) for 1 hr 30 min
  4. temperaturethe mixture is refluxed a further 30 min
  5. temperaturecooled to 20° C
  6. filtrationThe suspension is filtered
  7. washwashed with ethanol and heptane
  8. customThe solid product is dried under vacuum at a temperature of 60° C.
  9. customto obtain
  10. custom177 g (88% molar yield)

Sources & evidence

ORD record
ord-d2c939d3e43142f6bb6efdfb61eb20e4
Source dataset
uspto-grants-2009_10
Patent number
US07608711B2

Reaction notes

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