Pentane → HCID 178487765, compound

HRID 1852102Notes

Reaction equation

HRID 1852102 reaction equation
C([N:3]([CH2:15][CH3:16])[C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1C)C.C([Li])(C)(C)C.CCCCC.[CH3:27][N:28](C)[C:29]#N>C1COCC1>[CH3:27][N:28]([CH3:29])[C:15]1[N:3]=[C:4]([OH:14])[C:5]2[C:6]([CH:16]=1)=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=2

Participants

6

Reactant 4

HCID 8003PentaneHCID 15112DimethylcyanamideHCID 11053218N,N-diethyl-4-methoxy-2-methyl-benzamideHCID 178418306HCID 178418306, compound

Product 1

HCID 178487765HCID 178487765, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N,N-diethyl-4-methoxy-2-methylbenzamide (1000 mg, 4.52 mmol) in THF (10 ml) at −78° C. was added dropwise tert-butyllithium 1.7 M in pentane (5316 μl, 9.04 mmol) and the solution was stirred for 0.5 h before addition of N,N-dimethylcyanamide (317 mg, 4.52 mmol) in THF (10 ml). The resulting solution was warmed to rt and stirred for 16 h. The reaction mixture was quenched with water, neutralized with 1 N HCl, and extracted with EtOAc. The organic layer was collected, dried over sodium sulfate, filtered, followed by removal of solvent under vacuum to give 3-(dimethylamino)-6-methoxyisoquinolin-1-ol (700 mg, 71% yield) which was carried to the next step without further purification. MS: MS m/z 219.1 (M++1).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc
  3. customThe organic layer was collected
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customfollowed by removal of solvent under vacuum

Sources & evidence

ORD record
ord-94f59aa635db413dba8134ab2ecb9f93
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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