Acetic Acid → HCID 18448356, compound

HRID 1269639Notes

Reaction equation

HRID 1269639 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.[CH:10](=O)[CH2:11][CH3:12].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:5]=[CH:6][CH:7]=1)[NH:8][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 527PropanalHCID 1235383-Bromo-o-toluidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18448356HCID 18448356, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-2-methylphenylamine (1.5 g, 8.06 mmol) in dry CH2Cl2 with 3A molecular sieves was added propionaldehyde (580 μL, 8.06 mmol) and the resultant mixture stirred at room temperature for 20 min under nitrogen. Acetic acid (561 μL, 8.06 mmol) and sodium triacetoxyborohydride (4.78 g, 22.56 mmol) were added and the resultant mixture stirred under nitrogen at room temperature for 16 h. Saturated sodium bicarbonate (60 mL) was added portionwise and the resultant mixture stirred for 0.5 h and extracted with CH2Cl2 (2×100 mL). The organic solution was dried (Na2SO4) and the solvents removed in vacuo to afford the title compound as a yellow oil (1.8 g).

Workup

  1. extractionextracted with CH2Cl2 (2×100 mL)
  2. dry with materialThe organic solution was dried (Na2SO4)
  3. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-dba27708a1f448e09c51e0d40ad69ddf
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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