Acetic Acid → 4-(6,7-Dimethoxyquinolin-4-yloxy)-benzene-1,2-diamine

HRID 491670Notes

Reaction equation

HRID 491670 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][C:24]=1[N+:25]([O-])=O)[O:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=2)[N:11]=[CH:10][CH:9]=1)([O-])=O.CC(O)=O>C1COCC1.[Zn]>[CH3:19][O:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][C:14]=1[O:20][CH3:21])[N:11]=[CH:10][CH:9]=[C:8]2[O:7][C:6]1[CH:5]=[C:4]([NH2:1])[C:24]([NH2:25])=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 177563934-(3,4-Dinitrophenoxy)-6,7-dimethoxyquinoline

Product 1

HCID 177557264-(6,7-Dimethoxyquinolin-4-yloxy)-benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-(3,4-Dinitrophenoxy)-6,7-dimethoxyquinoline (Step a, 0.256 g) was dissolved in THF (40 mL) and HOAc (1 mL) was added followed by zinc dust (1.3 g). Mixture was stirred at RT for 3 h and filtered through a Celite® pad. Solvent was evaporated and residue was washed with NaOH 1 M and extracted with EtOAc. The organic phase was dried, filtered and evaporated to give the title compound.

Workup

  1. filtrationfiltered through a Celite® pad
  2. customSolvent was evaporated
  3. washresidue was washed with NaOH 1 M
  4. extractionextracted with EtOAc
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-d4157f11e9cf4ba3bdcd72ef2efdb90a
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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