Tetrahydrofuran → HCID 16733151, compound

HRID 370073Notes

Reaction equation

HRID 370073 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:29])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:19]=2[N+:26]([O-])=O)=[N:14][CH:15]=1.O1CCCC1.C(=O)([O-])[O-].[K+].[K+]>O.O1CCOCC1>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:29])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:19]=2[NH2:26])=[N:14][CH:15]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 16731657HCID 16731657, compound

Product 1

HCID 16733151HCID 16733151, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of sodium hydrosulfite (300 g, 1.7 mol) in water (4 L) was added N-(5-chloropyridin-2-yl)-2-nitro-3-methoxybenzamide (140 g, 0.45 mol). Tetrahydrofuran (2 L) and 1,4-dioxane (2 L) were added and the resulting mixture stirred at ambient temperature. After 16 hours, the solution was made basic by addition of potassium carbonate and the phases separated. The organic phase was concentrated of all volatiles in vacuo to give an off-white solid. The solid was washed with water, filtered, and dried under vacuum to afford 111 g (88% yield) of N-(5-chloropyridin-2-yl)-2-amino-3-methoxybenzamide; NMR (CDCl3) 8.8 (br, 1), 8.3 (d, 1), 8.1 (s, 1), 7.7 (dd, 1), 7.1 (dd, 1), 6.8 (d, 1), 6.6 (t, 1), 5.9 (br, 1), 3.9 (s, 3) ppm.

Workup

  1. customthe phases separated
  2. concentrationThe organic phase was concentrated of all volatiles in vacuo
  3. customto give an off-white solid
  4. washThe solid was washed with water
  5. filtrationfiltered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-9b3fbb640af34e989723f18fdc266dac
Source dataset
uspto-grants-2000_10
Patent number
US06140351

Reaction notes

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