HCID 5370806, compound → HCID 5369023, compound

HRID 879919Notes

Reaction equation

HRID 879919 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[CH:12]\[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-])=O)/[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1>O.[NH4+].[OH-].C1COCC1.S([O-])([O-])(=O)=O.[Fe+2]>[Br:1][C:2]1[CH:3]=[CH:4][C:5](/[C:8](=[CH:12]\[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH2:19])/[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 1

HCID 5370806HCID 5370806, compound

Product 1

HCID 5369023HCID 5369023, compound

Reagents, catalysts & solvents 4

HCID 24393Ferrous SulfateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14923Ammonium HydroxideSolvent2×

Procedure

506 g (1.8 mol) of iron (II) sulfate are initially introduced in 475 ml of water and 1000 ml of 25% NH4OH solution and heated to the boil. 79.3 g (228 mmol) of (E)-2-(4-bromophenyl)-3-(2-nitrophenyl)acrylic acid in a mixture of 150 ml of 10% NH4OH solution and 200 ml of THF are added dropwise over the course of 30 min, and the mixture is heated at the boil for a further 30 min. The reaction mixture is filtered hot through Celite, washed with warm 10% NH4OH solution and neutralised using acetic acid, and the resultant solid is filtered off with suction, washed with water and MeOH and dried. Yield of yellow, felt-like crystals: 52 g (72.3%).

Workup

  1. additionare added dropwise over the course of 30 min
  2. temperaturethe mixture is heated at the boil for a further 30 min
  3. filtrationThe reaction mixture is filtered hot through Celite
  4. washwashed
  5. temperaturewith warm 10% NH4OH solution
  6. filtrationthe resultant solid is filtered off with suction
  7. washwashed with water and MeOH
  8. customdried

Sources & evidence

ORD record
ord-2c72ab8aa15045c58341c7a9d05fe8e2
Source dataset
uspto-grants-2015_03
Patent number
US08993123B2

Reaction notes

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