4-Aminosalicylic Acid → 2-Hydroxy-4-(3-nitro-benzylamino)-benzoic acid

HRID 18440

反応式

HRID 18440 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[N+:26]([C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH:32]=O)([O-:28])=[O:27].[OH-].[Na+]>ClCCCl>[OH:11][C:4]1[CH:3]=[C:2]([NH:1][CH2:32][C:31]2[CH:34]=[CH:35][CH:36]=[C:29]([N+:26]([O-:28])=[O:27])[CH:30]=2)[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

参加物

6

反応物 4

HCID 46494-Aminosalicylic AcidHCID 74493-NitrobenzaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 103567472-Hydroxy-4-(3-nitro-benzylamino)-benzoic acid収率 55.5%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a solution of 4-amino salicylic acid (153 mg; 1 mmol) in 1,2-dichloroethane (4 mL) under argon atmosphere was added sodium triacetoxyborohydride (317 mg; 1.5 mmol) and 3-nitrobenzaldehyde (226 mg; 1.5 mmol). The mixture was stirred at room temperature under argon overnight after which time 1 M NaOH (sq.; 5 mL) was added and the two layers separated. The aqueous layer was acidified with 2 M HCl (aq) and the precipitate formed filtered off and dried to yield 160 mg (55%) of a yellowish powder with satisfactorily purity. Mp. 189° C. (decomposes); MS (ESI−): 287 (MH−).

後処理

  1. additionwas added
  2. customthe two layers separated
  3. customthe precipitate formed
  4. filtrationfiltered off
  5. customdried

出典と根拠

ORDレコード
ord-6c3a3826d5ca4eb28738775ac507f009
出典データセット
uspto-grants-2010_06
特許番号
US07741352B2

関連ノート

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