Water → HCID 178480426, compound

HRID 874467Notes

Reaction equation

HRID 874467 reaction equation
[CH3:1][N:2]1[C:15]2[C:6]([CH:7]=[CH:8][C:9]3[N:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[CH2:18][CH:17]=[C:11]4[NH:12][C:13](=[O:16])[C:14]=2[C:10]=34)=[C:5]([N+:26]([O-])=O)[CH:4]=[CH:3]1.[Cl-].[NH4+].O>O1CCCC1.C(O)C.[Zn]>[NH2:26][C:5]1[CH:4]=[CH:3][N:2]([CH3:1])[C:15]2[C:6]=1[CH:7]=[CH:8][C:9]1[N:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[CH2:18][CH:17]=[C:11]3[NH:12][C:13](=[O:16])[C:14]=2[C:10]=13

Participants

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 90387320HCID 90387320, compound

Product 1

HCID 178480426HCID 178480426, compoundYield 88.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 82c (0.09 g, 0.241 mmol), zinc dust (0.236 g, 3.62 mmol) and ammonium chloride (0.129 g, 2.411 mmol) in tetrahydrofuran (2.6 mL), ethanol (1.3 mL), and water (0.65 mL) was stirred at ambient temperature for 1 hour and then filtered to remove the solid. The filtrate was concentrated and then slurried in water. The solid was collected by filtration and dried in a vacuum oven at 70° C. to give 0.0732 g (88%) of the title compound as an impure mixture.

Workup

  1. filtrationfiltered
  2. customto remove the solid
  3. concentrationThe filtrate was concentrated
  4. filtrationThe solid was collected by filtration
  5. customdried in a vacuum oven at 70° C.

Sources & evidence

ORD record
ord-fbd840ef06414ca0800a1a6c30b16669
Source dataset
uspto-grants-2015_03
Patent number
US08980879B2

Reaction notes

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