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Ethanol → Tert-butyl 8-amino-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

HRID 1887722
ノート
印刷プレビュー

反応式

HRID 1887722 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-])=O)[CH:11]=1)[NH:8][C:7](=[O:15])[CH:6]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:5]2.C(O)C.C([O-])=O.[NH4+]>[Pd].O1CCCC1>[NH2:12][C:10]1[CH:11]=[CH:2][CH:3]=[C:4]2[C:9]=1[NH:8][C:7](=[O:15])[CH:6]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:5]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 702EthanolHCID 2723923Ammonium formateHCID 59620339Tert-butyl 6-bromo-8-nitro-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

生成物 1

HCID 59620337Tert-butyl 8-amino-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate収率 92.7%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒
HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
65 °C

実験手順

tert-Butyl 6-bromo-8-nitro-2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate (628 g) was added to ethanol (3.1 L), and the mixture was heated at 65° C. To the mixture, 10% Pd—C (water content: 53%) (67.1 g) and ammonium formate (1.03 kg) were sequentially added, and the resultant mixture was stirred for 10 minutes under heating and reflux. Tetrahydrofuran (2.5 L) was added to the reaction mixture so as to dissolve the precipitates, and undissolved matter was removed through filtration with Celite. The filtrate was concentrated under reduced pressure, and water was added to the residue. The formed precipitates were recovered through filtration. The thus-obtained solid was dried, whereby the title compound (418 g) was yielded as a powdery compound.

後処理

  1. temperatureunder heating
  2. temperaturereflux
  3. dissolutionto dissolve the precipitates, and undissolved matter
  4. customwas removed through filtration with Celite
  5. concentrationThe filtrate was concentrated under reduced pressure, and water
  6. additionwas added to the residue
  7. customThe formed precipitates
  8. filtrationwere recovered through filtration
  9. customThe thus-obtained solid was dried

出典と根拠

ORDレコード
ord-4fca78a441c04d61a50c9deeb4af89f3
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08501772B2

反応ノート

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