Ammonium Chloride → HCID 67235639, compound

HRID 1023569Notes

Reaction equation

HRID 1023569 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:11][C:12]2[N:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][N:13]=2)[CH:7]=[CH:8][C:9]=1[CH3:10])[CH3:2].C1COCC1.O.[Cl-].[NH4+]>[Fe].O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:11][C:12]2[N:17]=[CH:16][C:15]([NH2:18])=[CH:14][N:13]=2)[CH:7]=[CH:8][C:9]=1[CH3:10])[CH3:2]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 21881883Oxolane--water (1/1)HCID 67236723HCID 67236723, compound2×

Product 1

HCID 67235639HCID 67235639, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Fe powder (89 mg, 1.598 mmol) was added to a solution of 2-{[3-(ethyloxy)-4-methylphenyl]oxy}-5-nitropyrimidine (Intermediate 91, 110 mg) in a mixture THF/water (9 mL/3 mL) followed by ammonium chloride (86 mg, 1.598 mmol). The reaction mixture was stirred overnight under nitrogen. The reaction mixture was poured into water and the iron was filtrated. Ethyl acetate was used to wash the solid filtrated. The filtrate was extracted with ethyl acetate (3 times). The combined ethyl acetate layers were dried over sodium sulphate and concentrated to give the title compound (94 mg) which was directly used in the next step.

Workup

  1. filtrationthe iron was filtrated
  2. washto wash the solid
  3. filtrationfiltrated
  4. extractionThe filtrate was extracted with ethyl acetate (3 times)
  5. dry with materialThe combined ethyl acetate layers were dried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f98d11cfff804103b5886554ceedb716
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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