HCID 10156578、化合物 → 3-Amino-6-hydroxy-7-methoxynaphthalene-2-carboxylic acid tert-butyl ester

HRID 902411ノート

反応式

HRID 902411 の反応式
[C:1]([O:5][C:6]([C:8]1[C:17]([NH2:18])=[CH:16][C:15]2[C:10](=[CH:11][C:12]([O:27][CH3:28])=[C:13]([O:19]CC3C=CC=CC=3)[CH:14]=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CN(C=O)C.CO.C(Cl)Cl.[Pd]>[C:1]([O:5][C:6]([C:8]1[C:17]([NH2:18])=[CH:16][C:15]2[C:10](=[CH:11][C:12]([O:27][CH3:28])=[C:13]([OH:19])[CH:14]=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 1

HCID 10156578HCID 10156578、化合物

生成物 1

HCID 120627383-Amino-6-hydroxy-7-methoxynaphthalene-2-carboxylic acid tert-butyl ester収率 97.9%

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 4.7 g (12.0 mmol) of 3-amino-6-benzyloxy-7-methoxynaphthalene-2-carboxylic acid tert-butyl ester and 2.0 g of 10% Pd/C in 40 mL of DMF and 100 mL of methanol is shaken on Parr shaker at 40 psi for 18 hours. The hydrogenation is repeated twice more to bring the reaction to completion. The catalyst is filtered through a pad of Celite, is washed with methanol and solvent is evaporated to yield a residue which is dissolved in methylene chloride. This is then filtered through a short pad of Magnesol and is washed with methylene chloride and ethyl acetate. The filtrate is evaporated to yield 3.4 g of 3-amino-6-hydroxy-7-methoxy-naphthalene-2-carboxylic acid tert-butyl ester as a yellow solid, mp 262-263° C.

後処理

  1. customthe reaction to completion
  2. filtrationThe catalyst is filtered through a pad of Celite
  3. washis washed with methanol and solvent
  4. customis evaporated
  5. customto yield a residue which
  6. filtrationThis is then filtered through a short pad of Magnesol
  7. washis washed with methylene chloride and ethyl acetate
  8. customThe filtrate is evaporated

出典と根拠

ORDレコード
ord-3d4c7bc2450f49c294da761856928438
出典データセット
uspto-grants-2008_04
特許番号
US07365197B2

反応ノート

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