Hydrochloric Acid → HCID 66691674, compound

HRID 1051179Notes

Reaction equation

HRID 1051179 reaction equation
[CH:1]1([NH:4][C:5](=[O:22])[C:6]2[CH:11]=[CH:10][C:9]([B:12]3[O:16]C(C)(C)C(C)(C)[O:13]3)=[CH:8][C:7]=2[CH3:21])[CH2:3][CH2:2]1.I([O-])(=O)(=O)=O.[Na+].C([O-])(=O)C.[NH4+].Cl>CC(C)=O.O>[CH:1]1([NH:4][C:5]([C:6]2[CH:11]=[CH:10][C:9]([B:12]([OH:16])[OH:13])=[CH:8][C:7]=2[CH3:21])=[O:22])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 23667635Sodium periodateHCID 66691012HCID 66691012, compound

Product 1

HCID 66691674HCID 66691674, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of N-cyclopropyl-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (20.2 g, 67.13 mol) in acetone (300 mL) at rt was added sodium periodate (43.1 g, 201.40 mot) and ammonium acetate (134.26 mol, 134 mL 1M aqueous solution) and the mixture was stirred for 3 h. More water was added (120 mL), and the mixture was stirred at 40° C. for 2 h more. After addition of 4 N HCl (32 mL), the organic phase was removed in vaccuo and the reminder was extracted with ethyl actate. The organic phase was washed with saturated sodium chloride solution, filtered through a Whatman filter and evaporated. The residue was redissolved in toluene and evaporated (two times) to yield 14.59 g (94.3%) [4-(cyclopropylcarbamoyl)-3-methylphenyl]boronic acid.

Workup

  1. stirringthe mixture was stirred at 40° C. for 2 h more
  2. customthe organic phase was removed in vaccuo
  3. extractionthe reminder was extracted with ethyl actate
  4. washThe organic phase was washed with saturated sodium chloride solution
  5. filtrationfiltered through a Whatman
  6. filtrationfilter
  7. customevaporated
  8. dissolutionThe residue was redissolved in toluene
  9. customevaporated (two times)

Sources & evidence

ORD record
ord-fd56bec0909442a091009cb97bc7b2d3
Source dataset
uspto-grants-2016_07
Patent number
US09388140B2

Reaction notes

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