Sodium Hydroxide → HCID 70873862, compound

HRID 2208834Notes

Reaction equation

HRID 2208834 reaction equation
[CH2:1]([N:8]([CH2:21][CH3:22])[C:9]1[C:10]([CH3:20])=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12]([O:14]CC)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO>[CH2:1]([N:8]([CH2:21][CH3:22])[C:9]1[C:10]([CH3:20])=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70874194HCID 70874194, compound

Product 1

HCID 70873862HCID 70873862, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of ethyl 3-[benzyl(ethyl)amino]-2-methylbenzoate (370 mg, 1.24 mmol) in THF (20 ml) and MeOH (5 ml) was added 2M NaOH (3.11 ml, 6.22 mmol) and the reaction was stirred at 50° C. for 16 h. The reaction was cooled to room temperature and the solvent removed in vacuo after which the aqueous solution was adjusted to pH1 using 1M HCl. The product was extracted into DCM (3×50 ml), washed with brine (20 ml), dried with Na2SO4 concentrated and filtered to afford the title compound as an orange oil (296 mg, 80%) which was used in the next stage without any further purification. LC-MS 91%, m/z=270.0, 1H NMR (500 MHz, Chloroform-d) δ 7.73 (d, J=7.5 Hz, 1H), 7.34-7.30 (m, 4H), 7.23 (dt, J=15.4, 6.9 Hz, 3H), 4.12 (d, J=13.5 Hz, 2H), 3.04-2.94 (m, 2H), 2.69 (s, 3H), 0.99 (t, J=7.0 Hz, 3H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe solvent removed in vacuo after which the aqueous solution
  3. extractionThe product was extracted into DCM (3×50 ml)
  4. washwashed with brine (20 ml)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated
  7. filtrationfiltered

Sources & evidence

ORD record
ord-5f72d9527be94db5bd09f5eb7ff3adac
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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