Methyl Isocyanate → HCID 18963976, compound

HRID 2226952Notes

Reaction equation

HRID 2226952 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH2:21][CH2:22][NH:23][OH:24])[CH:16]=3)[C:11]2=[O:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:26][N:27]=[C:28]=[O:29]>O1CCOCC1.CCOC(C)=O>[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH2:21][CH2:22][N:23]([C:28]([NH:27][CH3:26])=[O:29])[OH:24])[CH:16]=3)[C:11]2=[O:25])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 18963940HCID 18963940, compound

Product 1

HCID 18963976HCID 18963976, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

2-(3-Phenylpropyl)-6-[2-(N-hydroxyamino)-ethoxy]-1-oxo-1,2,3,4-tetrahydroisoquinoline (498 mg, 1.5 mmol) is dissolved in dioxane t 15 mL) and methyl isocyanate (0.22 mL, 3.7 mmol) is added. After 12 hours, the reaction mixture is diluted with EtOAc (150 mL) and the organic phase washed with 2N HCl (2×200 mL), H2O (4×200 mL), saturated NaHCO3 solution (2×200 mL), saturated NaCl solution (2×200 mL), dried over MgSO4 and concentrated in vacuo. The resulting material is triturated with hexanes and recrystallized from CH2C2 /hexanes to give 2-(3-phenylpropyl)-6-{2-[N-(methylaminocarbonyl)-N-hydroxyamino]-ethoxy}-1-oxo-1,2,3,4-tetrahydroisoquinoline, m.p. 138°-139°.

Workup

  1. additionis added
  2. washthe organic phase washed with 2N HCl (2×200 mL), H2O (4×200 mL), saturated NaHCO3 solution (2×200 mL), saturated NaCl solution (2×200 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting material is triturated with hexanes
  6. customrecrystallized from CH2C2 /hexanes

Sources & evidence

ORD record
ord-d3d136aaab224e9d963f6b11e6f73644
Source dataset
uspto-grants-1994_09
Patent number
US05350761

Reaction notes

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