Sodium amide → 2-Amino-5-fluoro-3-hydroxy-4-picoline

HRID 2397845Notes

Reaction equation

HRID 2397845 reaction equation
[NH2-].[Na+].[NH2:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([F:11])=[CH:6][N:5]=1.N(C1C=C(C)C(F)=CN=1)[N+]([O-])=[O:14]>>[NH2:3][C:4]1[C:9]([OH:14])=[C:8]([CH3:10])[C:7]([F:11])=[CH:6][N:5]=1

Participants

4

Reactant 3

HCID 24533Sodium amideHCID 214366762-Nitramino-5-fluoro-4-picolineHCID 220636705-Fluoro-4-methylpyridin-2-amine

Product 1

HCID 214366682-Amino-5-fluoro-3-hydroxy-4-picoline

Procedure

When 3-amino-4-picoline is subjected to diazotization in fluoboric acid as in Example I-1, there is obtained 3-fluoro-4-picoline. Treatment of the latter intermediate with sodium amide as in Example I-1, gives 2-amino-5-fluoro-4-picoline. Following the procedure of Example I-15, but substituting 2-nitramino-5-fluoro-4-picoline, there is obtained 2-amino-5-fluoro-4-methyl-3-pyridinol.

Sources & evidence

ORD record
ord-e378e522988748669335e6028b0ba3bc
Source dataset
uspto-grants-1977_05
Patent number
US04022897

Reaction notes

Loading…