Tetrahydrofuran → HCID 67010729, compound

HRID 2194541Notes

Reaction equation

HRID 2194541 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[O:12]1[CH2:17][CH2:16][O:15][C:14]2[CH:18]=[C:19]([NH:22][C:23]3[N:32]=[CH:31][CH:30]=[CH:29][C:24]=3[C:25](OC)=[O:26])[CH:20]=[CH:21][C:13]1=2.[OH-].[Na+]>C(OCC)(=O)C>[O:12]1[CH2:17][CH2:16][O:15][C:14]2[CH:18]=[C:19]([NH:22][C:23]3[C:24]([CH2:25][OH:26])=[CH:29][CH:30]=[CH:31][N:32]=3)[CH:20]=[CH:21][C:13]1=2

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67009517HCID 67009517, compound

Product 1

HCID 67010729HCID 67010729, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen gas stream, 1.70 g (41 mmol) of lithium aluminum hydride was added to tetrahydrofuran (100 mL) under ice cooling, and a tetrahydrofuran (30 mL) solution of 9.86 g (34 mmol) of methyl 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)aminonicotinate was added dropwise to the mixture. Ethyl acetate was added to the reaction mixture, and subsequently, 17 mL of a 10% aqueous solution of sodium hydroxide was added thereto. Insoluble materials were filtered off. The filtrate was concentrated, and the residue was dissolved in ethyl acetate, dried, filtered, and concentrated. Thus, 8.9 g of the title compound was obtained as an orange-colored viscous product (yield: quantitative).

Workup

  1. filtrationInsoluble materials were filtered off
  2. concentrationThe filtrate was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4fd65915757d468d88faa505c8ddb6b4
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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