Hydrochloric Acid → HCID 21518600, compound

HRID 1283663Notes

Reaction equation

HRID 1283663 reaction equation
[OH:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][C:9]=2[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)=[O:7])=[CH:4][CH:3]=1.Cl>>[NH2:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][C:9]2[O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:8]=2[C:6](=[O:7])[C:5]2[CH:27]=[CH:28][C:2]([OH:1])=[CH:3][CH:4]=2)=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 21518635HCID 21518635, compound

Product 1

HCID 21518600HCID 21518600, compound

Procedure

3-(4'-Hydroxybenzoyl)-2-(4'-nitrobenzyl)benzofuran (37.3 g., 0.1 mol.) is added in small portions to 56.4 g. (0.25 mol.) of stannous chloride dihydrate in 70 ml. of concentrated hydrochloric acid. The reaction mixture is heated at 50° for 3 hours, then stirred at 25° for 12 hours. Cooling (ice bath) enhances precipitation of the product salt which is collected by filtration and dissolved in water. The aqueous solution is made basic by addition of 10% aqueous sodium hydroxide and extracted with chloroform. The extracts are dried (MgSO4) and concentrated to give 2-(4'-aminobenzyl)-3-(4'-hydroxybenzoyl)benzofuran.

Workup

  1. temperatureThe reaction mixture is heated at 50° for 3 hours
  2. temperatureCooling (ice bath)
  3. customprecipitation of the product salt which
  4. filtrationis collected by filtration
  5. dissolutiondissolved in water
  6. additionThe aqueous solution is made basic by addition of 10% aqueous sodium hydroxide
  7. extractionextracted with chloroform
  8. dry with materialThe extracts are dried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e74968bdb505495eb59b639ca75a0a88
Source dataset
uspto-grants-1976_08
Patent number
US03975537

Reaction notes

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