Ammonium Chloride → HCID 61305676, compound

HRID 626403Notes

Reaction equation

HRID 626403 reaction equation
[Br:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][NH:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]=2[N+:18]([O-])=O)=[CH:4][CH:3]=1.[NH4+].[Cl-]>CO.C1COCC1.[Zn]>[NH2:18][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:8]=1[NH:7][CH2:6][C:5]1[CH:21]=[CH:22][C:2]([Br:1])=[CH:3][CH:4]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 24902937HCID 24902937, compound

Product 1

HCID 61305676HCID 61305676, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(4-bromobenzylamino)-3-nitrobenzoate (1 g, 2.73 mmol) in methanol (10 mL) and THF (15 mL) was added sat. NH4Cl aqueous solution (15 mL), then zinc powder (2.11 g, 27.3 mmol) was added in one portion. The mixture was stirred at RT for 1 hr. Then the solid was filtered and the filtrate was concentrated. The residue was washed with water (20 mL) and EtOAc (30 mL×3), the combined organic layers were concentrated to the titled compound which was used to the next step without further purification.

Workup

  1. filtrationThen the solid was filtered
  2. concentrationthe filtrate was concentrated
  3. washThe residue was washed with water (20 mL) and EtOAc (30 mL×3)
  4. concentrationthe combined organic layers were concentrated to the titled compound which
  5. customwas used to the next step without further purification

Sources & evidence

ORD record
ord-3a96d41199a64a3e8bb00b16e765ff6d
Source dataset
uspto-grants-2016_04
Patent number
US09309227B2

Reaction notes

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