Hydrochloric Acid → 2-(4-Bromo-3-formyl-phenoxy)-6-[(2-hydroxy-ethyl)-methyl-amino]-nicotinonitrile

HRID 1664384Notes

Reaction equation

HRID 1664384 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][OH:18])[CH:12]=[CH:11][C:8]=2[C:9]#[N:10])=[CH:4][C:3]=1[CH:21]1[O:25]CCO1.Cl.[CH2:27]1COCC1>>[Br:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[N:14]=[C:13]([N:15]([CH2:16][CH2:17][OH:18])[CH3:27])[CH:12]=[CH:11][C:8]=2[C:9]#[N:10])=[CH:4][C:3]=1[CH:21]=[O:25]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 674405562-(4-Bromo-3-[1,3]dioxolan-2-yl-phenoxy)-6-(2-hydroxy-ethylamino)-nicotinonitrile

Product 1

HCID 866364302-(4-Bromo-3-formyl-phenoxy)-6-[(2-hydroxy-ethyl)-methyl-amino]-nicotinonitrileYield 55%

Procedure

To a solution of 6 (2-(4-bromo-3-[1,3]dioxolan-2-yl-phenoxy)-6-(2-hydroxy-ethylamino)-nicotinonitrile, 1.1 g, 2.7 mmol) in THF (200 mL) was added a HCl solution (1 M, 100 mL). The reaction was stirred at room temperature overnight. The THF was evaporated in vacuo. The white solid that formed was filtered and air-dried to afford 0.94 g (55% yield for two steps) of the title compound.

Workup

  1. customThe THF was evaporated in vacuo
  2. customThe white solid that formed
  3. filtrationwas filtered
  4. customair-dried

Sources & evidence

ORD record
ord-40c710ef4b0947af881cfab3d55e6ddb
Source dataset
uspto-grants-2011_10
Patent number
US08039450B2

Reaction notes

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