Ammonium Chloride → t-Butyl 5-amino-2-(6-cyano-2-naphthyloxy)benzoate

HRID 895715Notes

Reaction equation

HRID 895715 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([O:13][C:14]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:7]=[CH:6]2)#[N:2].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:27][C:24]1[CH:25]=[CH:26][C:14]([O:13][C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([C:1]#[N:2])[CH:4]=3)[CH:9]=2)=[C:15]([CH:23]=1)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 22380917t-Butyl 2-(6-cyano-2-naphthyloxy)-5-nitrobenzoate

Product 1

HCID 22380961t-Butyl 5-amino-2-(6-cyano-2-naphthyloxy)benzoate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

The compound (t-butyl 2-(6-cyano-2-naphthyloxy)-5-nitrobenzoate) (760 mg) obtained in a previous production example, iron powder (718 mg) and ammonium chloride (73 mg) were heated to reflux in ethanol:water (3:1, 30 ml) and reacted for 30 minutes. The insoluble portion was immediately filtered using celite, and the filtrate was concentrated. A saturated sodium bicarbonate solution was added to the obtained residue, and extraction was performed with ethyl acetate. The ethyl acetate layer was washed with saturated saline and then dried over magnesium sulfate, and the solvent was distilled off to obtain 736 mg of t-butyl 5-amino-2-(6-cyano-2-naphthyloxy)benzoate.

Workup

  1. temperaturewere heated
  2. customreacted for 30 minutes
  3. filtrationThe insoluble portion was immediately filtered
  4. concentrationthe filtrate was concentrated
  5. additionA saturated sodium bicarbonate solution was added to the obtained residue, and extraction
  6. washThe ethyl acetate layer was washed with saturated saline
  7. dry with materialdried over magnesium sulfate
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-cba85a63da3e417ba2d78b997d74018d
Source dataset
uspto-grants-2005_07
Patent number
US06916837B2

Reaction notes

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