Acetic Acid → 2-Amino-4-(quinolin-4-yloxy)-phenol

HRID 491664Notes

Reaction equation

HRID 491664 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[OH:21])([O-])=O.CC(O)=O>C1COCC1.[Zn]>[NH2:1][C:4]1[CH:9]=[C:8]([O:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[OH:21]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 177550132-Nitro-4-(quinolin-4-yloxy)-phenol

Product 1

HCID 177558402-Amino-4-(quinolin-4-yloxy)-phenol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Nitro-4-(quinolin-4-yloxy)-phenol (Step A, 200 mg) was dissolved in THF (50 mL) at 0° C. and AcOH (0.88 mL) was added followed by zinc dust (2.3 g). The mixture was stirred at RT for 1.5 h and filtered through a Celite® 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 solid.

Workup

  1. filtrationfiltered through a Celite® 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-f107deebce384abe9268a7da09b248ed
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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