3-Chloro-2-[4-(1-methylethylamino)-3-nitrophenyl]-5-trifluoromethylpyridine → 2-[3-Amino-4-(1-methylethylamino)phenyl]-3-chloro-5-trifluoromethylpyridine

HRID 1276079Notes

Reaction equation

HRID 1276079 reaction equation
ClC1C(C2C=CC(O)=C(N)C=2)=NC=C(C(F)(F)F)C=1.[Cl:20][C:21]1[C:22]([C:31]2[CH:36]=[CH:35][C:34]([NH:37][CH:38]([CH3:40])[CH3:39])=[C:33]([N+:41]([O-])=O)[CH:32]=2)=[N:23][CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1>[Fe]>[NH2:41][C:33]1[CH:32]=[C:31]([C:22]2[C:21]([Cl:20])=[CH:26][C:25]([C:27]([F:30])([F:29])[F:28])=[CH:24][N:23]=2)[CH:36]=[CH:35][C:34]=1[NH:37][CH:38]([CH3:40])[CH3:39]

Participants

4

Reactant 2

HCID 221148393-Chloro-2-[4-(1-methylethylamino)-3-nitrophenyl]-5-trifluoromethylpyridineHCID 1355499702-Amino-4-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]benzenol

Product 1

HCID 221148412-[3-Amino-4-(1-methylethylamino)phenyl]-3-chloro-5-trifluoromethylpyridineYield 93%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

In a similar manner to the preparation of 3-chloro-2-(3-amino-4-hydroxyphenyl)-5-trifluoromethylpyridine described above, 46.1 g of 3-chloro-2-[4-(1-methylethylamino)-3-nitro-phenyl]-5-trifluoromethylpyridine and 21.5 g of iron powder gave 39.1 g (93%) of colorless crystals; m.p.: 116-117° C.

Sources & evidence

ORD record
ord-37082797aeaf483f8bc329006fb6fe6e
Source dataset
uspto-grants-2000_12
Patent number
US06165941

Reaction notes

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