Sodium Hydroxide → 4,5-Difluoropyridin-2-amine

HRID 717560Notes

Reaction equation

HRID 717560 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([NH:9]C(=O)C(C)(C)C)[CH:3]=1.[OH-].[Na+]>Cl>[F:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([NH2:9])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86729659N-(4,5-difluoropyridin-2-yl)-2,2-dimethylpropanamide

Product 1

HCID 717433744,5-Difluoropyridin-2-amine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N-(4,5-difluoropyridin-2-yl)-2,2-dimethylpropanamide (47-2; 0.380 g) in concentrated HCl was heated at 95° C. for 5 h. The reaction mixture was cooled to RT, diluted with ice cold water (20 mL) and basified with 10% aqueous sodium hydroxide solution. The reaction mixture was extracted with ethyl acetate (2×50 mL). The combined organic layers were dried over sodium sulphate and concentrated under vacuum to afford the title compound. 1H NMR (400 MHz, DMSO) δ 7.72-7.67 (m, 1H), 6.59-6.55 (m, 1H), 6.48 (bs, 2H).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (2×50 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b4b3293e37d641bda96414702ddc8cef
Source dataset
uspto-grants-2015_11
Patent number
US09193724B2

Reaction notes

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