Ammonium Chloride → 2-Ethoxy-4-aminobenzoic acid

HRID 2263949

反応式

HRID 2263949 の反応式
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2].[Cl-].[NH4+]>C(O)C.[Fe]>[NH2:13][C:11]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:3][CH2:1][CH3:2])[CH:12]=1

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 27363472-Ethoxy-4-nitrobenzoic acid

生成物 1

HCID 101763852-Ethoxy-4-aminobenzoic acid収率 88.1%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

2-Ethoxy-4-nitrobenzoic acid (20 g, 94 mmol, Aldrich) was suspended in ethanol (170 mL) and combined with a saturated aqueous solution of ammonium chloride (100 mL). As this was rapidly stirred, iron dust (13.3 g, 239 mmol) was added in portions. The temperature was raised to 80° C. for 1 h. The cooled suspension was filtered through Celite, and the cake washed with dichloromethane (150 mL). The filtrate was diluted with dichloromethane and washed with brine, dried over magnesium sulfate, filtered and evaporated. A brown solid was triturated with dichloromethane and filtered to give 15 g of 4-amino-2-ethoxybenzoic acid (88%).

後処理

  1. filtrationThe cooled suspension was filtered through Celite
  2. washthe cake washed with dichloromethane (150 mL)
  3. additionThe filtrate was diluted with dichloromethane
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customA brown solid was triturated with dichloromethane
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-6840192751e7404f86f9691611b22422
出典データセット
uspto-grants-2010_12
特許番号
US07851626B2

関連ノート

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