Acetic Acid → 4-(Quinolin-4-yloxy)-benzene-1,2-diamine

HRID 491655Notes

Reaction equation

HRID 491655 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][C:20]=1[N+:21]([O-])=O)[O:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][CH:9]=1)([O-])=O.CC(O)=O>C1COCC1.[Zn]>[N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([O:7][C:6]2[CH:5]=[C:4]([NH2:1])[C:20]([NH2:21])=[CH:19][CH:18]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 177560764-(3,4-Dinitro-phenoxy)-quinoline

Product 1

HCID 177564934-(Quinolin-4-yloxy)-benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-(3,4-Dinitro-phenoxy)-quinoline (Step A, 400 mg, 1.2 mmol) was dissolved in THF at 0° C., and AcOH (1.5 mL) was added followed by zinc dust (2.5 g, 38 mmol). The mixture was stirred at RT for 1 h then filtered on a silica pad. The solvent was evaporated; the residue was dissolved in CH2Cl2 and washed with 1M NaOH. The organic phases were dried, filtered and evaporated to give the title compound, as a brown-orange oil.

Workup

  1. filtrationthen filtered on a silica pad
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in CH2Cl2
  4. washwashed with 1M NaOH
  5. customThe organic phases were dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-61b125cd162e40d9b2e9ae3062281b9d
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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