Tetrahydrofuran → HCID 67010052, compound

HRID 2194530Notes

Reaction equation

HRID 2194530 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[CH3:12][C:13]1[O:17][N:16]=[C:15]([NH:18][C:19]2[N:28]=[CH:27][CH:26]=[CH:25][C:20]=2[C:21](OC)=[O:22])[CH:14]=1.[OH-].[Na+]>C(OCC)(=O)C>[CH3:12][C:13]1[O:17][N:16]=[C:15]([NH:18][C:19]2[C:20]([CH2:21][OH:22])=[CH:25][CH:26]=[CH:27][N:28]=2)[CH:14]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67009927HCID 67009927, compound

Product 1

HCID 67010052HCID 67010052, compoundYield 108.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen gas stream, 0.75 g (20 mmol) of lithium aluminum hydride was added to tetrahydrofuran (70 mL) under ice cooling, and a tetrahydrofuran (30 mL) solution of 2.3 g (9.9 mmol) of methyl 2-(5-methyl-3-isoxazolyl)aminonicotinate was added dropwise to the above solution. The resulting mixture was stirred for one hour under ice cooling. Ethyl acetate was added to the reaction mixture, and 8.0 mL of a 10% aqueous solution of sodium hydroxide was further added thereto. Insoluble materials were filtered off. The filtrate was concentrated, and the residue was dissolved in ethyl acetate, dried, filtered, and concentrated. Thus, 2.2 g of the title compound was obtained as an orange-colored viscous product (yield: quantitative).

Workup

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

Sources & evidence

ORD record
ord-6fb22c65001b452996c206519050bd2b
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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