Ammonium Chloride → HCID 68873015, compound

HRID 1770843Notes

Reaction equation

HRID 1770843 reaction equation
[C:1]([CH2:3][O:4][C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[C:7]([O:14][CH3:15])[C:6]=1[O:16][CH3:17])#[N:2].[Cl-].[NH4+]>C(O)C.C(Cl)Cl.[Fe]>[C:1]([CH2:3][O:4][C:5]1[CH:10]=[C:9]([CH:8]=[C:7]([O:14][CH3:15])[C:6]=1[O:16][CH3:17])[NH2:11])#[N:2]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 68873326HCID 68873326, compound

Product 1

HCID 68873015HCID 68873015, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.4 g of 1-cyanomethoxy-2,3-dimethoxy-5-nitrobenzene in 75 mL ethanol with 1.65 g of iron and 1.65 g of ammonium chloride was refluxed for 4 h, cooled to RT, diluted with DCM, filtered, extracted with DCM and the combined organic were dried with sodium sulfate and evaporated to give 1 g 82% of the desired product 3-cyanomethoxy-4,5-dimethoxyaniline, MS (m/e): 209 (MH+).

Workup

  1. filtrationfiltered
  2. extractionextracted with DCM
  3. dry with materialthe combined organic were dried with sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-aa04d0d5700b487a8d2ccfb04b16a2c0
Source dataset
uspto-grants-2016_02
Patent number
US09248190B2

Reaction notes

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