Acetic Acid → Dimethyl 5-(diethylamino)isophthalate

HRID 2071128Notes

Reaction equation

HRID 2071128 reaction equation
[CH:1](=O)[CH3:2].[NH2:4][C:5]1[CH:6]=[C:7]([C:15]([O:17][CH3:18])=[O:16])[CH:8]=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11].[BH3-]C#N.[Na+].[CH3:23][C:24](O)=O>CC#N.O>[CH2:23]([N:4]([CH2:1][CH3:2])[C:5]1[CH:14]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=[C:7]([CH:6]=1)[C:15]([O:17][CH3:18])=[O:16])[CH3:24]

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 177AcetaldehydeHCID 66831Dimethyl 5-aminoisophthalateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 59570097Dimethyl 5-(diethylamino)isophthalateYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Acetaldehyde (1.07 ml, 0.8 g, 19.12 mmol, 8 eq) was added to a stirred solution of dimethyl 5-aminoisophthalate (0.500 g, 2.39 mmol, 1 eq) in CH3CN (15 ml) and water (0.5 ml) at 0° C. After 10 min NaBH3CN (0.395 g, 5.98 mmol, 2.5 eq) was added. The reaction was adjusted to pH {tilde over ( )} 7 with HOAc. After 1.5 h the reaction was adjusted to pH {tilde over ( )} 7 with HOAc a second time. The reaction was stirred at 0° C. to room temperature overnight. The solvent was removed in vacuo, and the residue was dissolved in EtOAc. The organic layer was washed with saturated aqueous NaHCO3 (×2), water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.575 g (2.17 mmol, 91% yield) of the product.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe organic layer was washed with saturated aqueous NaHCO3 (×2), water (×3), brine (×1)
  4. dry with materialdried over Na2SO4
  5. filtrationThe inorganics were filtered off
  6. customthe solvent was removed in vacuo
  7. customPurification via flash chromatography

Sources & evidence

ORD record
ord-f92fd876bcea402b993769746d7c93d7
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

Loading…