Ammonium Chloride → HCID 61307255, compound

HRID 1520304Notes

Reaction equation

HRID 1520304 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH3:16])=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7])([O-])=O.[NH4+].[Cl-]>CO.O.[Fe]>[NH2:1][C:4]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH3:16])=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67298168HCID 67298168, compound

Product 1

HCID 61307255HCID 61307255, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 2-nitro-5-propoxy-benzamide (1.20 g, 5.36 mmol) in MeOH-H2O (v/v, 3:1, 60 mL) was added NH4Cl (2.84 g, 53.6 mmol) and Fe (2.99 g, 53.6 mmol). The resulting mixture was stirred at 60° C. for 3 h. After the reaction was completed, the mixture was cooled to room temperature and the iron was filtered off. The filtrate was concentrated to 15 mL and the formed precipitate was collected and dried in vacuo to give 1.02 g of ii-a as a pale yellow solid (98%). LCMS m/z=1781 (M−16), 195.1 (M+1) (Method B) (retention time=1.46 min).

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. filtrationthe iron was filtered off
  3. concentrationThe filtrate was concentrated to 15 mL
  4. customthe formed precipitate was collected
  5. customdried in vacuo

Sources & evidence

ORD record
ord-6ae4e64deacb49e9b830afddb9cb8b13
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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