Hydrochloric Acid → (5-Bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amine

HRID 1357270ノート

反応式

HRID 1357270 の反応式
[BH4-].[Na+].[Br:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([CH:16]=[N:17][CH3:18])=[CH:9]2.Cl>C(O)C>[Br:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([CH2:16][NH:17][CH3:18])=[CH:9]2

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 18505272(5-Bromo-6-methoxy-naphthalen-2-ylmethylene)-methyl-amine

生成物 1

HCID 18505315(5-Bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amine収率 94%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Sodium borohydride (131 mg, 3.47 mmol) was added under nitrogen to a warm solution of (5-bromo-6-methoxy-naphthalen-2-ylmethylene)-methyl-amine (950 mg, 4.41 mmol), prepared in the previous step, in 30 mL of absolute ethanol. After the addition the reaction was stirred at room temperature for 19 h (overnight). 1 N HCl was added dropwise until the reaction was pH˜1 (litmus paper). The solvent was removed under reduced pressure and the residue partitioned between methylene chloride and water. The aqueous layer was made basic by the addition of 1 N NaOH. The organic layer was separated and the aqueous layer was extracted three times with methylene chloride. The combined extracts were dried (MgSO4) and the solvent removed under reduced pressure to give (5-bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amine (900 mg, 94%) as an off-white solid, mp 41-45° C.

後処理

  1. additionAfter the addition the reaction
  2. customThe solvent was removed under reduced pressure
  3. customthe residue partitioned between methylene chloride and water
  4. additionThe aqueous layer was made basic by the addition of 1 N NaOH
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted three times with methylene chloride
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. customthe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-bbceb141f3374b4e85e5c9b7cfdfe4eb
出典データセット
uspto-grants-2003_07
特許番号
US06589970B2

反応ノート

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