Triethylamine → 4-([(6-Methoxypyridin-3-yl)methylene]amino}benzene-1,3-diol

HRID 2241821Notes

Reaction equation

HRID 2241821 reaction equation
Cl.[NH2:2][C:3]1[CH:9]=[CH:8][C:6]([OH:7])=[CH:5][C:4]=1[OH:10].C(N(CC)CC)C.[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][N:21]=1>CO>[CH3:18][O:19][C:20]1[N:21]=[CH:22][C:23]([CH:24]=[N:2][C:3]2[CH:9]=[CH:8][C:6]([OH:7])=[CH:5][C:4]=2[OH:10])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 33645766-Methoxypyridine-3-carbaldehydeHCID 134088224-Aminobenzene-1,3-diol hydrochloride

Product 1

HCID 592038424-([(6-Methoxypyridin-3-yl)methylene]amino}benzene-1,3-diol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Aminoresorcinol hydrochloride (3.09 mmol) and triethylamine (3.25 mmol) were dissolved in dry methanol (20 mL). 6-Methoxynicotinaldehyde (3.09) was added and the mixture was stirred overnight. The solvents were removed under reduced pressure, the mixture diluted with EtOAc, washed with brine (2×), dried (Na2SO4), filtered and evaporated to give 1.31 g as a dark solid. The crude product was taken to the next step without further purification. MS m/z (M+H) 245.

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionthe mixture diluted with EtOAc
  3. washwashed with brine (2×)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give 1.31 g as a dark solid
  8. customThe crude product was taken to the next step without further purification

Sources & evidence

ORD record
ord-472d4c255d49435e873579756197c59b
Source dataset
uspto-grants-2010_03
Patent number
US07670591B2

Reaction notes

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