Tetrahydrofuran → (2-Anilinopyridin-3-yl)methanol

HRID 2194525Notes

Reaction equation

HRID 2194525 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[C:12]1([NH:18][C:19]2[N:27]=[CH:26][CH:25]=[CH:24][C:20]=2[C:21](O)=[O:22])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>C(OCC)(=O)C>[C:12]1([NH:18][C:19]2[C:20]([CH2:21][OH:22])=[CH:24][CH:25]=[CH:26][N:27]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 14817992-Anilinonicotinic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 13986159(2-Anilinopyridin-3-yl)methanolYield 108.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Under a nitrogen gas stream, 2.41 g (63.4 mmol) of lithium aluminum hydride was added to tetrahydrofuran (80 mL) under ice cooling, and a tetrahydrofuran (30 mL) solution of 6.79 g (31.7 mmol) of 2-(phenylamino)nicotinic acid was added dropwise to the above solution. The resulting mixture was stirred for 2 hours at room temperature. Ethyl acetate was added to the reaction mixture, and 25 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 thus obtained was dissolved in ethyl acetate, dried, filtered, and concentrated. Thus, 6.9 g of the title compound was obtained as a yellow viscous product (yield: quantitative).

Workup

  1. additionwas further added
  2. filtrationInsoluble materials were filtered off
  3. concentrationThe filtrate was concentrated
  4. customthe residue thus obtained
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-05ffb3b666654e4e944b06fc396c8e6c
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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