Ammonium Chloride → (4-Amino-3-benzylamino-phenyl)-carbamic acid tert-butyl ester

HRID 930541Notes

Reaction equation

HRID 930541 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[C:10]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>C(O)C.O.[Fe]>[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 117892034(3-Benzylamino-4-nitro-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 117889326(4-Amino-3-benzylamino-phenyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of (3-benzylamino-4-nitro-phenyl)-carbamic acid tert-butyl ester E-1.5′ (5.000 g; 15 mmol) in ethanol (50.000 g) is added a solution of ammonium chloride (3.932 g, 73 mmol) in water (10 ml). The reaction mixture is then stirred at 70° C. for 20 min Iron powder (4.077 g; 73 mmol) is then added portionwise and the reaction is stirred for 4 h at reflux. The reaction mixture is filtered and washed with hot ethanol. The filtrate is concentrated under reduced pressure. Water is added and the mixture is extracted with 10% MeOH in DCM. The combined organic layer is dried over Na2SO4 and concentrated under reduced pressure. The product is used in the next step without further purification.

Workup

  1. additionis then added portionwise
  2. temperatureat reflux
  3. filtrationThe reaction mixture is filtered
  4. washwashed with hot ethanol
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. additionWater is added
  7. extractionthe mixture is extracted with 10% MeOH in DCM
  8. dry with materialThe combined organic layer is dried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe product is used in the next step without further purification

Sources & evidence

ORD record
ord-d6a67480b23d4585a39ae941be855323
Source dataset
uspto-grants-2016_03
Patent number
US09296748B2

Reaction notes

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