Ammonium Chloride → HCID 90103494, compound

HRID 1052467Notes

Reaction equation

HRID 1052467 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[OH:16].[Cl-].[NH4+]>C1COCC1.O.C(=O)([O-])[O-].[Na+].[Na+].[Fe]>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:17])=[C:8]([OH:16])[CH:9]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 90102721HCID 90102721, compound

Product 1

HCID 90103494HCID 90103494, compoundYield 24%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 10340Sodium CarbonateSolvent

Procedure

2-(3-(Dimethylamino)propoxy)-5-nitrophenol (220 mg 0.92 mmol), ammonium chloride (232 mg, 4.34 mmol) and powdered iron (242 mg, 4.33 mmol) were suspended in THF (5 ml) and water (10 ml) and the mixture was stirred at 70° C. overnight. The reaction mixture was diluted with water, neutralised to pH=6 with sodium carbonate and extracted with ethyl acetate (×3). The organic phase was washed successively with water and brine, dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure. 75 mg (24% yield, 61% purity) of the title compound were obtained and used in the next synthetic step without further purification.

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. washThe organic phase was washed successively with water and brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-14cd4919f28c4a9aadbc7b2719daeb62
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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