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Formamide → 5-(3-amino-2-methoxy-phenyl)-1,2,4-trimethyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 384305
ノート
印刷プレビュー

反応式

HRID 384305 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH3:11])=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[C:13]=2[O:21][CH3:22])[N:8]([CH3:23])[C:7]=1[CH3:24])=[O:5])[CH3:2].C(N)=O>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH3:11])=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[C:13]=2[O:21][CH3:22])[N:8]([CH3:23])[C:7]=1[CH3:24])=[O:5])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 713FormamideHCID 596156595-(3-nitro-2-methoxy-phenyl)-1,2,4-trimethyl-1H-pyrrole-3-carboxylic acid ethyl ester

生成物 1

HCID 596156885-(3-amino-2-methoxy-phenyl)-1,2,4-trimethyl-1H-pyrrole-3-carboxylic acid ethyl ester収率 86%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

5-(3-Nitro-2-methoxy-phenyl)-1,2,4-trimethyl-1H-pyrrole-3-carboxylic acid ethyl ester 6f (300 mg, 0.9 mmol) was dissolved in 5 mL of ethyl acetate followed by addition of formamide (227 mg, 1.61 mmol) and 60 mg of palladium on carbon. The reaction mixture was heated to reflux for 1 hour. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filter cake was washed with ethyl acetate. The filtrate was concentrated under reduced pressure to obtain the title compound 5-(3-amino-2-methoxy-phenyl)-1,2,4-trimethyl-1H-pyrrole-3-carboxylic acid ethyl ester 6g (234 mg, yield 86%) as a white solid.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. filtrationThe mixture was filtered
  4. washthe filter cake was washed with ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-c87bf086ddfb4a22bb6200dcaf648899
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08367710B2

反応ノート

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