Ammonium Chloride → HCID 59667325, compound

HRID 1671503Notes

Reaction equation

HRID 1671503 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[S:15][CH:14]=[C:13]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[CH:19]=3)[C:8]=2[C:9](Cl)=[N:10][CH:11]=1)=[O:5])[CH3:2].[NH4+].[Cl-]>O1CCOCC1.C1COCC1.CN(C=O)C.O.C(OCC)(=O)C.[Zn]>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[S:15][CH:14]=[C:13]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=3)[C:8]=2[CH:9]=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

9

Reactant 2

HCID 25517Ammonium ChlorideHCID 58832946HCID 58832946, compound

Product 1

HCID 59667325HCID 59667325, compound

Reagents, catalysts & solvents 6

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 4-chloro-3-(3-nitro-phenoxymethyl)-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (398 mg, 1.01 mmol) (from Example 2 supra) in 1,4-dioxane (20 mL), THF (10 mL) and DMF (10 mL) was added NH4Cl (810 mg, 15.14 mmol) in water (6 mL). Zinc powder (783 mg, 12 mmol) was then added in several portions and the reaction was stirred at room temperature for a total of 4 hours. The resulting mixture was diluted with ethyl acetate (800 mL), washed with water (100 mL) and then brine (100 mL), dried (Na2SO4) and concentrated. The residue was purified by column chromatography (hexanes/EtOAc, 60/40 to 30/70) to give 3-(3-amino-phenoxymethyl)-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester as a white solid. (Yield 339.1 mg, 100%).

Workup

  1. washwashed with water (100 mL)
  2. dry with materialbrine (100 mL), dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (hexanes/EtOAc, 60/40 to 30/70)

Sources & evidence

ORD record
ord-23a9520262ec4f4098fbc84a5565a4aa
Source dataset
uspto-grants-2011_08
Patent number
US07994321B2

Reaction notes

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