Ammonium Hydroxide → HCID 178494696, compound

HRID 1620263Notes

Reaction equation

HRID 1620263 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([O:14][CH3:15])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH4+:16].[OH-].C[O:19][CH2:20][C:21](OC(=O)COC)=O>CCOCC.O>[CH3:10][O:9][C:8]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[C:11]([CH2:12][O:14][CH3:15])=[N:16][C:20]([OH:19])=[CH:21]2

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 85213Benzeneacetic acid, 3,4-dimethoxy-, methyl ester2×HCID 88095Methoxyacetic anhydride

Product 1

HCID 178494696HCID 178494696, compoundYield 2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of methyl 2-(3,4-dimethoxy-phenyl)acetate SLA 28134 (3.36 g, 15.98 mmol) in methoxyacetic anhydride SMA 44010 (10.19 g, 62.85 mmol) at 0° C. in a 250 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise HClO4 (ca. 70% solution in water, 1.64 mL, 18.98 mmol). The mixture was then stirred for 45 min at RT then diluted with Et2O (151 mL). The organic solution was removed to give a viscous residue that was suspended in H2O (30 mL) at 5° C. before dropwise addition of a conc. NH4OH solution (38 mL). After complete addition, the mixture was stirred overnight at RT and extracted with CH2Cl2 (50 mL) then with CH2Cl2:MeOH=95:5 (100 mL). The organic phase was combined, washed with brine (30 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum. Purification by column chromatography (SiO2, eluent CH2Cl2:MeOH=100:0 to 93:7) gave 6,7-dimethoxy-1-methoxymethyl-isoquinolin-3-ol SMA 44012 as a yellow solid (96 mg, 2% yield).

Workup

  1. customThe organic solution was removed
  2. customto give a viscous residue that
  3. additionAfter complete addition
  4. stirringthe mixture was stirred overnight at RT
  5. extractionextracted with CH2Cl2 (50 mL)
  6. washwashed with brine (30 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated at 40° C. under vacuum
  10. customPurification by column chromatography (SiO2, eluent CH2Cl2:MeOH=100:0 to 93:7)

Sources & evidence

ORD record
ord-14c6b8b7adec4f028d9a3c6954a68369
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

Loading…