Acetic Acid → HCID 67256828, compound

HRID 333558Notes

Reaction equation

HRID 333558 reaction equation
[C:1]1([NH:7][C:8]2[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][C:16]([CH3:18])=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH:16]([NH:14][C:13]1[C:8]([NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:9][CH:10]=[CH:11][CH:12]=1)([CH3:18])[CH3:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 106790912-N-phenylpyridine-2,3-diamine

Product 1

HCID 67256828HCID 67256828, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N2-phenylpyridine-2,3-diamine (14.1 g, 76 mmol) and acetone (8.39 mL, 114 mmol) was added to a solution of acetic acid and dichloromethane. Sodium triacetoxyborohydride (22.59 g, 107 mmol) was added to the reaction mixture and stirred overnight at room temperature. Reaction mixture was quenched with 1N HCl. Organic layer was extracted with ethyl acetate. Ethyl acetate solution was washed with 1N sodium hydroxide solution followed by brine and dried over anhd. MgSO4. N3-isopropyl-N2-phenylpyridine-2,3-diamine (16.3 g, 94% yield) was isolated from crude by column chromatography using hexanes and ethyl acetate as eluent.

Workup

  1. customReaction mixture
  2. customwas quenched with 1N HCl
  3. extractionOrganic layer was extracted with ethyl acetate
  4. washEthyl acetate solution was washed with 1N sodium hydroxide solution
  5. customdried over anhd

Sources & evidence

ORD record
ord-41efd6e102bc46eaba74404da236c66b
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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