Hydrochloric Acid → HCID 70873753, compound

HRID 2208856Notes

Reaction equation

HRID 2208856 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:14]([CH3:21])[CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([N:14]([CH3:21])[CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70873976HCID 70873976, compound

Product 1

HCID 70873753HCID 70873753, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 5-chloro-2-methoxy-3-[methyl(oxan-4-yl)amino]benzoate (413 mg, 1.32 mmol) in THF (13 ml) and MeOH (2 ml) was added 4M NaOH (13.16 ml). The reaction mixture was stirred at 50° C. for 16 hours. The reaction mixture was acidified to pH 2-3 with 6M HCl and extracted with DCM (5×10 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give 385 mg (98%) of the title compound as a thick yellow oil. LC-MS 94%, m/z=300.0/302.0, 1H NMR (500 MHz, Chloroform-d) δ ppm 7.74 (d, J=2.0 Hz, 1H), 7.30-7.12 (m, 1H), 4.11-4.02 (m, 2H), 4.01 (s, 3H), 3.54 (t, J=11.6 Hz, 1H), 3.40 (t, J=11.3 Hz, 2H), 2.76 (s, 3H), 1.97-1.78 (m, 2H), 1.63 (d, J=11.8 Hz, 2H).

Workup

  1. extractionextracted with DCM (5×10 ml)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1e2a900e79f9431b8ab6df6c0c1c753a
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

Loading…