4-Aminophenol → HCID 506617, compound

HRID 392404Notes

Reaction equation

HRID 392404 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=O)[CH:10]=1.[BH4-].[Na+]>CO.C(O)C>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][CH2:15][C:11]2[CH:10]=[N:9][CH:14]=[CH:13][CH:12]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 103713-PyridinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 506617HCID 506617, compound

Reagents, catalysts & solvents 1

HCID 18681192Ethanol, mixt. with methanolSolvent

Conditions

Temperature
0 °C

Procedure

Alternately, a solution of 4-aminophenol (1.0 equiv.) (Aldrich) in 2:1 methanol/ethanol was treated with 3-pyridinecarboxaldehyde (1.05 equiv.). The solution was allowed to stir for 1 hour. The reaction was cooled to 0° C. and treated with sodium borohydride (4.2 equiv.) in 5 portions. The cooling bath was removed and stirring continued for 20 hours. The reaction mixture was concentrated in vacuo. The residue was mixed with 1M HCl, warmed, and partitioned between ethyl acetate and 0.1M K2CO3. The pH of the aqueous phase was adjusted to pH=7 (using 1M HCl and 1M K2CO3) and the product extracted 4-6 times with ethyl acetate. The organic phases were combined, washed with brine, dried over anhydrous MgSO4, and concentrated to afford N-(4-hydroxyphenyl)pyridin-3-ylmethylamine. 1H NMR(400 MHz, DMSO-d6): d 4.18(2H, s), 5.65(1H, s), 6.41-6.53(4H, m), 7.29-7.32(1H, m), 7.70-7.72(1H, m), 8.39-8.40(2H, m), 8.53-8.54(1H, m). MS Found 201.2 [M+H]+.

Workup

  1. customThe cooling bath was removed
  2. stirringstirring
  3. waitcontinued for 20 hours
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. additionThe residue was mixed with 1M HCl
  6. temperaturewarmed
  7. custompartitioned between ethyl acetate and 0.1M K2CO3
  8. extractionthe product extracted 4-6 times with ethyl acetate
  9. washwashed with brine
  10. dry with materialdried over anhydrous MgSO4
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-971f16c272cb45a687177fa3489a05ba
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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