Hydrochloric Acid → 6-Amino-4-[3-chloro-4-(2-pyridylmethoxy)anilino]quinazoline

HRID 1397060ノート

反応式

HRID 1397060 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([N+:27]([O-])=O)[CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.Cl>C(O)C.O.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([NH2:27])[CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

参加物

6

反応物 2

HCID 313Hydrochloric AcidHCID 18967699N-[3-chloro-4-(2-pyridylmethoxy)phenyl]-6-nitro-quinazolin-4-amine

生成物 1

HCID 189676876-Amino-4-[3-chloro-4-(2-pyridylmethoxy)anilino]quinazoline収率 54.1%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

N-[3-Chloro-4-(2-pyridylmethoxy)phenyl]-6-nitro-quinazolin-4-amine 4d (4.07 g, 10 mmol) and concentrated hydrochloric acid (2 mL, 24 mmol) were dissolved in 130 mL of the solvent mixture of 95% ethanol and water (V/V=10/3), followed by addition of iron powder (11.17 g, 200 mmol). The reaction mixture was heated to reflux for 2 hours, filtered while hot and the filtrate was concentrated under reduced pressure to remove ethanol. The resulting residue was adjusted to pH>7 with ammonium hydroxide, filtered and the filter cake was dried under vacuum, purified by silica gel column chromatography with elution system A to obtain the title compound N4-[3-chloro-4-(2-pyridylmethoxy)phenyl]quinazoline-4,6-diamine 4e (2.04 g, yield 54.1%) as a white solid.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationfiltered while hot and the filtrate
  4. concentrationwas concentrated under reduced pressure
  5. customto remove ethanol
  6. filtrationfiltered
  7. customthe filter cake was dried under vacuum
  8. custompurified by silica gel column chromatography with elution system

出典と根拠

ORDレコード
ord-26a4e6101bc5440489256698ee0becf9
出典データセット
uspto-grants-2014_12
特許番号
US08901140B2

反応ノート

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