Acetic Acid → HCID 68205836, compound

HRID 333554Notes

Reaction equation

HRID 333554 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11]3[C:16]([NH2:17])=[CH:15][CH:14]=[CH:13][N:12]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:18][C:19]([CH3:21])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11]3[C:16]([NH:17][CH:19]([CH3:21])[CH3:18])=[CH:15][CH:14]=[CH:13][N:12]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 12445395HCID 12445395, compound

Product 1

HCID 68205836HCID 68205836, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The N2-(benzo[d][1,3]dioxol-5-yl)pyridine-2,3-diamine (8.5 g, 37.1 mmol) was dissolved in dichloromethane (150 mL). Acetone (4.1 mL, 55.6 mmol), sodium triacetoxyborohydride (11.79 g, 55.6 mmol) and acetic acid (4.2 mL, 74.2 mmol) were added to it. This was stirred at ambient temperature for 18 h. The mixture was washed with 1N NaOH and then washed with water. The organic layer was concentrated in vacuo and chromatographed using a gradient of 0-10% ethyl acetate in dichloromethane to give N2-(benzo[d][1,3]dioxol-5-yl)-N3-isopropylpyridine-2,3-diamine (7.8 grams, 78%).

Workup

  1. washThe mixture was washed with 1N NaOH
  2. washwashed with water
  3. concentrationThe organic layer was concentrated in vacuo
  4. customchromatographed

Sources & evidence

ORD record
ord-528027ebd2364c01afd75fe7735c57ea
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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