Ammonium Chloride → Ethyl 5-amino-4-methoxythiophene-2-carboxylate

HRID 59754ノート

反応式

HRID 59754 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:6][C:7]=1[N+:8]([O-])=O.[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:8][C:7]1[S:6][C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][C:3]=1[O:2][CH3:1]

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 86703861Ethyl 4-methoxy-5-nitrothiophene-2-carboxylate

生成物 1

HCID 86703860Ethyl 5-amino-4-methoxythiophene-2-carboxylate

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 19096565Water ethanol溶媒

反応条件

温度
50 °C

実験手順

A mixture of ethyl 4-methoxy-5-nitrothiophene-2-carboxylate (Int. 68) (300 mg, 1.297 mmol) (prepared as described in Step 4 hereabove reported), and ammonium chloride (139 mg, 2.59 mmol) in EtOH/water=2/1 (18 ml) was heated at 50° C. until complete dissolution. Iron powder (435 mg, 7.78 mmol) was added, and the reaction was heated at 80° C. for 2 hours. The mixture was filtered and the filtrate was concentrated under vacuum; the residue was portioned between brine and EtOAc and the organic phase was dried over sodium sulfate. The solvent was removed to afford ethyl 5-amino-4-methoxythiophene-2-carboxylate (Int. 69) in a mixture with approximately 30% of corresponding methyl ester (261 mg, 1.297 mmol, MS/ESI+201.9 [MH]+). This intermediate was used as such in the following step.

後処理

  1. temperaturethe reaction was heated at 80° C. for 2 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under vacuum
  4. dry with materialthe organic phase was dried over sodium sulfate
  5. customThe solvent was removed

出典と根拠

ORDレコード
ord-1f953e59a22b4bf3927beb31b17e41b5
出典データセット
uspto-grants-2016_09
特許番号
US09440954B2

反応ノート

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