Phosphoric Acid → Benzenamine, 2-ethyl-6-methoxy-

HRID 1955145Notes

Reaction equation

HRID 1955145 reaction equation
[N+:1]([C:4]1[C:9]([CH:10](O)[CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=1[O:13][CH3:14])([O-])=O.OP(O)(O)=O>C1COCC1.[Pd]>[CH2:10]([C:9]1[CH:8]=[CH:7][CH:6]=[C:5]([O:13][CH3:14])[C:4]=1[NH2:1])[CH3:11]

Participants

5

Reactant 2

HCID 1004Phosphoric AcidHCID 10104161HCID 10104161, compound

Product 1

HCID 10080569Benzenamine, 2-ethyl-6-methoxy-Yield 43%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 27B (310 mg) was dissolved in 10 mL of THF; 1.5 mL of H3PO4 was added, followed by 50 mg of 10% palladium-on-charcoal. The resultant mixture was purged with nitrogen, then placed under a balloon of hydrogen, and stirred overnight. Bicarb was added carefully, and the mixture was filtered through a pad of Celite. The filtrate was extracted with EtOAc; the organic extracts were washed with bicarb and brine, and were concentrated in vacuo. The crude product was purified by flash chromatography on silica gel, eluting with 1:1 ether/hexanes, to give 102 mg (43% yield) of the title compound as a colorless oil.

Workup

  1. customThe resultant mixture was purged with nitrogen
  2. additionBicarb was added carefully
  3. filtrationthe mixture was filtered through a pad of Celite
  4. extractionThe filtrate was extracted with EtOAc
  5. washthe organic extracts were washed with bicarb and brine
  6. concentrationwere concentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica gel
  8. washeluting with 1:1 ether/hexanes

Sources & evidence

ORD record
ord-4e2b6c1c4eca4b1fa51c900f5c7bcebd
Source dataset
uspto-grants-2000_09
Patent number
US06124341

Reaction notes

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