Acetic Acid → 31143-05-2

HRID 499233Notes

Reaction equation

HRID 499233 reaction equation
C([BH3-])#N.[Na+].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=1.[CH3:14][C:15]([CH3:17])=O.C(O)(=O)C>CO.C(Cl)Cl>[CH:15]([NH:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][CH3:5])[CH:8]=1)([CH3:17])[CH3:14]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 108243-MethoxyanilineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 1908490831143-05-2

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a microwave tube charged with a stirring bar was added sodium cyanoborohydride (0.10 g, 1.6 mmol) and m-anisidine (0.075 mL, 0.8 mmol) in methanol (1 mL). To this solution was the added acetone (0.5 mL) and glacial acetic acid (0.5 mL). Once the gas evolution had subsided, the tube was crimped and subjected to microwave irradiation at 130° C. for 15 minutes. The solution was diluted with CH2Cl2, washed once with 1N NaOH, and the organic layer was dried (Na2SO4), filtered and concentrated to a yellow liquid. This was purified via silica gel chromatography with an ethyl acetate/hexanes gradient (Rf=0.60 in 4:1 Hex/EtOAc) to give N-isopropyl-3-methoxybenzenamine as a colorless oil. FIA MS 166 (M+1).

Workup

  1. additionTo a microwave tube charged with a stirring bar
  2. customirradiation at 130° C. for 15 minutes
  3. washwashed once with 1N NaOH
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow liquid
  7. customThis was purified via silica gel chromatography with an ethyl acetate/hexanes gradient (Rf=0.60 in 4:1 Hex/EtOAc)

Sources & evidence

ORD record
ord-551046f75b9448c5aeda2e16d5c6442e
Source dataset
uspto-grants-2010_08
Patent number
US07767680B2

Reaction notes

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