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

HRID 384305
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HRID 384305 반응식
[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]
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c87bf086ddfb4a22bb6200dcaf648899
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08367710B2

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