Lithium hydroxide, monohydrate → Ammonium Hydroxide

HRID 1921163Notes

Reaction equation

HRID 1921163 reaction equation
Br[CH2:2][C:3]1[C:8]([CH2:9]Br)=[CH:7][N:6]=[C:5]([C:11]#[N:12])[CH:4]=1.[NH:13]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[CH2:15][C:14]1=[O:22].O.[OH-].[Li+]>C1COCC1.O>[NH4+:6].[OH-:22].[O:22]=[C:14]1[NH:13][C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[C:15]21[CH2:9][C:8]1[CH:7]=[N:6][C:5]([C:11]#[N:12])=[CH:4][C:3]=1[CH2:2]2

Participants

7

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 138640951,3-Dihydro-2H-pyrrolo(2,3-b)pyridin-2-oneHCID 57417127HCID 57417127, compound

Product 2

HCID 14923Ammonium HydroxideHCID 57974054HCID 57974054, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,5-bis(bromomethyl)pyridine-2-carbonitrile from Step B (2.56 g, 8.83 mmol) and 1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [Marfat & Carta (1987) Tetrahedron Lett. 28, 4027] (1.18 g, 8.83 mmol) in THF (120 mL) and H2O (60 mL) was added lithium hydroxide monohydrate (1.11 g, 26.5 mmol). After 20 min, the reaction mixture was poured onto water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH: NH4OH—100:0:0 to 95:5:1, to give the title compound. MS: m/z=263 (M+1).

Workup

  1. additionthe reaction mixture was poured onto water (100 mL)
  2. extractionextracted with EtOAc (3×100 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-4ae24a5d845c42fe83d74ac295005110
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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