2-Amino-5-chloropyridine → HCID 178425984, compound

HRID 1054963Notes

Reaction equation

HRID 1054963 reaction equation
[C:1]1([CH3:14])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O:12][NH2:13])(=[O:11])=[O:10].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([NH2:22])=[N:20][CH:21]=1>C(Cl)Cl>[CH3:8][C:3]1[CH:4]=[C:5]([CH3:7])[CH:6]=[C:1]([CH3:14])[C:2]=1[S:9]([O-:12])(=[O:11])=[O:10].[NH2:13][N:20]1[CH:21]=[C:16]([Cl:15])[CH:17]=[CH:18][C:19]1=[NH2+:22]

Participants

4

Reactant 2

HCID 661742-Amino-5-chloropyridineHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 178425984HCID 178425984, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The fresh solution of O-(mesitylsulfonyl)hydroxylamine (2.14 g, 9.96 mmol, Eq: 1.00) in CH2Cl2 prepared in the previous step was added dropwise at 0° C. to a solution of 5-chloropyridin-2-amine (1.28 g, 9.96 mmol, Eq: 1.00) in CH2Cl2 (20 ml). The suspension was stirred for 20 min and then filtered. The residue was washed with DCM and dried under high vacuum to give the desired product as a white powder (2.5 g, 73%). MS m/z=144.03 (M−MsO+H+)

Workup

  1. filtrationfiltered
  2. washThe residue was washed with DCM
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-a5ef53d3e5d7428f94e4ccb3a70a0f69
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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