Ethanol → HCID 178497567, compound

HRID 2243091Notes

Reaction equation

HRID 2243091 reaction equation
S(=O)(O)[O-].[Na+].[C:6]([C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)([OH:8])=[O:7].[NH2:17][C:18]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:19]=1[NH2:20].[CH2:28](O)C>O.CN(C=O)C>[N+:25]([C:22]1[CH:23]=[CH:24][C:18]2[NH:17][C:13]([C:12]3[CH:15]=[CH:16][C:9]([C:6]([O:8][CH3:28])=[O:7])=[CH:10][CH:11]=3)=[N:20][C:19]=2[CH:21]=1)([O-:27])=[O:26]

Participants

7

Reactant 4

HCID 702EthanolHCID 120884-Formylbenzoic acidHCID 51117914-Nitro-1,2-phenylenediamineHCID 23665763Sodium Bisulfite

Product 1

HCID 178497567HCID 178497567, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium bisulfite (7.0 g, 0.036 mol) in water (70 ml) is added to 4-carboxybenzaldehyde (11.0 g, 0.071 mol) in ethanol (70 ml). The mixture is stirred at room temperature for 15 minutes, the solid is filtered off, the filtrate is coevaporated with toluene and a solution of 2-amino-5-nitroaniline (11.1 g, 0.071 mol) in DMF (250 ml) is added. This mixture is refluxed for 3 hours and concentrated, and the product is recrystallized from dilute HCl, filtered off and washed with water. The solid is suspended in methanol (300 ml) and HCl gas is bubbled through at 5-15° C. for 3 hours. The mixture is allowed to warm to room temperature and is then refluxed for 3 hours. The solution is concentrated to 1/3 of its volume and cooled to +5° C., and the precipitate is filtered off and recrystallized from NaHCO3 and finally from 3/1 isopropyl ether/hexane. Yield: 15 g (71%); IR (KBr): 3570, 3472, 3112, 1707, 1301 cm−1; 1H-NMR (d6-DMSO) 7.7-8.5 (m, 7H); 5.9 (m, 1H); 3.88 (s, 3H).

Workup

  1. filtrationthe solid is filtered off
  2. temperatureThis mixture is refluxed for 3 hours
  3. concentrationconcentrated
  4. customthe product is recrystallized from dilute HCl
  5. filtrationfiltered off
  6. washwashed with water
  7. customHCl gas is bubbled through at 5-15° C. for 3 hours
  8. temperatureto warm to room temperature
  9. temperatureis then refluxed for 3 hours
  10. concentrationThe solution is concentrated to 1/3 of its volume
  11. temperaturecooled to +5° C.
  12. filtrationthe precipitate is filtered off
  13. customrecrystallized from NaHCO3 and finally from 3/1 isopropyl ether/hexane

Sources & evidence

ORD record
ord-d5e439f5ddc740eca1f6193e4d523cef
Source dataset
uspto-grants-2010_03
Patent number
US07674809B2

Reaction notes

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