Aluminium lithium hydride → HCID 136336334, compound

HRID 2218260Notes

Reaction equation

HRID 2218260 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[N:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[OH:27])[CH:18]=[C:17]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([NH2:34])[CH:29]=2)[C:9]=1[C:10](OC(C)(C)C)=[O:11]>C1COCC1>[NH2:7][C:8]1[N:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[OH:27])[CH:18]=[C:17]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([NH2:34])[CH:29]=2)[C:9]=1[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 136336331HCID 136336331, compound

Product 1

HCID 136336334HCID 136336334, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold (0° C.) suspension of lithium aluminum hydride (0.077 g, 1.62 mmol) in THF (3 mL) under an argon atmosphere was added dropwise a solution of tert-butyl 2-amino-4-(3-aminophenyl)-6-(2-hydroxyphenyl)nicotinate (0.353 g, 0.935 mmol) in THF (2 mL) with stirring. After 30 minutes, the mixture was allowed to warm to room temperature, and the stirring was continued at room temperature for 2 hrs. and at 50° C. overnight. After cooled to room temperature, the reaction mixture was quenched with water and extracted with ethyl acetate. The separated organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by recrystallization from methanol to give 2-[6-amino-4-(3-aminophenyl)-5-(hydroxymethyl)-2-pyridinyl]phenol as a pale yellow solid (0.133 g, yield 45%).

Workup

  1. waitthe stirring was continued at room temperature for 2 hrs
  2. customat 50° C.
  3. customovernight
  4. temperatureAfter cooled to room temperature
  5. customthe reaction mixture was quenched with water
  6. extractionextracted with ethyl acetate
  7. washThe separated organic phase was washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by recrystallization from methanol

Sources & evidence

ORD record
ord-cd2ae17fd19d49d3aaa6e27cad27f3ac
Source dataset
uspto-grants-2008_08
Patent number
US07410986B2

Reaction notes

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