Methylamine → 2-Methoxy-5-[(methylamino)methyl]phenol

HRID 2236638ノート

反応式

HRID 2236638 の反応式
[CH3:1][NH2:2].[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH:7]=O.[BH4-].[Na+]>C(O)C>[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:6]([CH2:7][NH:2][CH3:1])=[CH:5][C:4]=1[OH:3]

参加物

5

反応物 3

HCID 6329MethylamineHCID 12127IsovanillinHCID 4311764Sodium borohydride

生成物 1

HCID 15199372-Methoxy-5-[(methylamino)methyl]phenol収率 75%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Methylamine (40% aqueous solution, 2.2 mL, 25 mmol) is added to a solution of 3-hydroxy-4-methoxybenzaldehyde (3.0 g, 20 mmol) in ethanol (35 mL). The resulting slurry is stirred for 30 minutes at room temperature. Then the solvents were evaporated under reduced pressure. The resulting solid is dissolved in methanol (300 mL) and sodium borohydride (0.90 g, 24 mmol) is added. The reaction mixture is stirred for 2 hours at room temperature and then concentrated under reduced pressure. The residue is partitioned between saturated aqueous potassium carbonate solution and ethyl acetate. The aqueous phase is extracted 3× with ethyl acetate, and the combined extracted were concentrated under reduced pressure to give 2-methoxy-5-methylaminomethyl-phenol as a granular white solid (2.5 g, 75%).

後処理

  1. customThen the solvents were evaporated under reduced pressure
  2. dissolutionThe resulting solid is dissolved in methanol (300 mL)
  3. stirringThe reaction mixture is stirred for 2 hours at room temperature
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is partitioned between saturated aqueous potassium carbonate solution and ethyl acetate
  6. extractionThe aqueous phase is extracted 3× with ethyl acetate
  7. extractionthe combined extracted
  8. concentrationwere concentrated under reduced pressure

出典と根拠

ORDレコード
ord-cad3046dac7742998d9af4d3c41014f0
出典データセット
uspto-grants-2010_05
特許番号
US07713994B2

反応ノート

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