Sodium hydride → HCID 90095750, compound

HRID 927272Notes

Reaction equation

HRID 927272 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:27])[CH2:12][C:13]2[CH:22]=[C:21]([C:23]([O:25][CH3:26])=[O:24])[CH:20]=[CH:19][C:14]=2[C:15](OC)=[O:16])=[CH:6][CH:5]=1>O1CCCC1.C(OCC)(=O)C>[F:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:11](=[O:27])[CH2:12][C:13]3[C:14](=[CH:19][CH:20]=[C:21]([C:23]([O:25][CH3:26])=[O:24])[CH:22]=3)[C:15]2=[O:16])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 90094671HCID 90094671, compound

Product 1

HCID 90095750HCID 90095750, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

NaH (0.382 g, 9.56 mmol) was added to a stirred, 0° C. mixture of dimethyl 2-(2-((4-fluorophenyl)amino)-2-oxoethyl)terephthalate (1.65 g, 4.78 mmol) in tetrahydrofuran (100 mL) and the mixture was stirred at 0° C. for 90 min. which turned into a red solution. The mixture was diluted with ethyl acetate (30 mL), washed with hydrochloric acid (0.5 M, 1×15 mL), water (10 mL), and brine (20 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure to give methyl 2-(4-fluorophenyl)-1,3-dioxo-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (1.5 g, 4.79 mmol) as a white solid.

Workup

  1. washwashed with hydrochloric acid (0.5 M, 1×15 mL), water (10 mL), and brine (20 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2df02788650d4affbf447d9c34e1242d
Source dataset
uspto-grants-2016_03
Patent number
US09290454B2

Reaction notes

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