Sodium Hydroxide → HCID 14853263, compound

HRID 2402826Notes

Reaction equation

HRID 2402826 reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[Cl:13])[C:3](O)=[O:4].B.C1COCC1.[OH-].[Na+]>>[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[Cl:13])[CH2:3][OH:4]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 2772346amino(2,3-dichlorophenyl)acetic acid

Product 1

HCID 14853263HCID 14853263, compound

Procedure

Quantities of 1.0 g (4.54 mmol) of amino-(2,3-dichlorophenyl)acetic acid and 18.18 ml (18.18 mmol) of borane-THF complex (1M solution in THF) were stirred together at RT until the reaction was complete. For work-up, pieces of ice were added. After the end of the evolution of gas, the mixture was adjusted to a pH of 9-10 using 1M aqueous sodium hydroxide solution, and extracted three times with tert-butyl methyl ether. The combined organic phases were dried over sodium sulphate, filtered and freed from the solvent on a rotary evaporator. Drying in an HV gave 880 mg (91% of theory) of the title compound.

Workup

  1. additionFor work-up, pieces of ice were added
  2. extractionextracted three times with tert-butyl methyl ether
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. filtrationfiltered
  5. customfreed from the solvent on a rotary evaporator
  6. customDrying in an HV

Sources & evidence

ORD record
ord-9cb787c07bd8457380b355e7c0e94694
Source dataset
uspto-grants-2014_08
Patent number
US08796324B2

Reaction notes

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