Water → HCID 18005159, compound

HRID 1977755Notes

Reaction equation

HRID 1977755 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[C:7]2[O:11][CH2:10][CH2:9][C:8]=2[CH:12]=1)([O-])=O.[Sn].O.[OH-].[Na+]>C(O)C.Cl>[NH2:1][C:4]1[CH:5]=[C:6]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[C:7]2[O:11][CH2:10][CH2:9][C:8]=2[CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 5352426Tin atom2×HCID 18005129HCID 18005129, compound

Product 1

HCID 18005159HCID 18005159, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

2,3-Dihydro-5-nitro-7-(pyrid-3-yl)benzofuran (D63) (0.19 g, 0.00079 mole) in ethanol (20 ml) was treated with a solution of tin II chloride (0.75 g, 0.0040 mole) in conc. hydrochloric acid (1 ml) and heated at 50° C for 2 hours. A further 0.38 g tin II chloride in conc. hydrochloric acid (0.5 ml) was added and the mixture was heated at 50° C. for ½ hour and stirred at ambient temperature for 18 hours. Deionised water (5 ml) was added and the mixture was basified with 10% sodium hydroxide solution, extracted into ethyl acetate, dried (Na2SO4) and evaporated in vacuo to afford the title compound (0.13 g, 82%) as a dark oil.

Workup

  1. temperaturethe mixture was heated at 50° C. for ½ hour
  2. extractionextracted into ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-ce2aeaa23bcc46d08af37027e747f9b6
Source dataset
uspto-grants-2001_05
Patent number
US06235758B1

Reaction notes

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