HCID 86615013, compound → 5-(1-Hydroxyethyl)-N-methyl-N-propyl-isophthalamic acid ethyl ester

HRID 732565Notes

Reaction equation

HRID 732565 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:17]=[C:16]([CH:18]=[O:19])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2].[CH3:21][Mg]Br>C1COCC1>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:17]=[C:16]([CH:18]([OH:19])[CH3:21])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 86615013HCID 86615013, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 688153185-(1-Hydroxyethyl)-N-methyl-N-propyl-isophthalamic acid ethyl esterYield 59.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Treat a solution of 5-formyl-N-methyl-N-propyl-isophthalamic acid ethyl ester (400 mg, 1.44 mmol) in THF (10 mL) at 0° C. with methylmagnesium bromide (3.0 M in diethyl ether, 0.58 mL, 1.73 mmol). Stir at 0° C. for 1 h and quench with saturated aqueous ammonium chloride solution. Extract with ethyl acetate (100 mL), dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 40:60 to 70:30 ethyl acetate:hexanes) to give the title compound (250 mg, 59%).

Workup

  1. customquench with saturated aqueous ammonium chloride solution
  2. extractionExtract with ethyl acetate (100 mL)
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 40:60 to 70:30 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-a35ab8fdb5864cc8bc7a88fbac9f2a5d
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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