Nitrogen → N-(2-(Dimethylamino)ethyl)acridine-4-carboxamide

HRID 1873070

反応式

HRID 1873070 の反応式
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]([C:15]([O:17]C)=O)=[CH:3][CH:2]=1.[CH3:19][N:20]([CH3:24])[CH2:21][CH2:22][NH2:23].N#N>C(O)CC>[CH3:19][N:20]([CH3:24])[CH2:21][CH2:22][NH:23][C:15]([C:4]1[C:5]2[C:14](=[CH:13][C:12]3[C:7]([N:6]=2)=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:1]=[CH:2][CH:3]=1)=[O:17]

参加物

5

反応物 3

HCID 947NitrogenHCID 66053N,N-DimethylethylenediamineHCID 11064418Methyl Acridine-4-carboxylate

生成物 1

HCID 107805N-(2-(Dimethylamino)ethyl)acridine-4-carboxamide収率 64.9%

試薬・触媒・溶媒 1

HCID 10311-Propanol溶媒

実験手順

A solution of methyl acridine 4-carboxylate (1.83 g, 7.72 mmol) and N,N-dimethylethylenediamine (3.40 g, 38.6 mmol) in n-propanol (80 ml) was flushed with N2, and the mixture was heated at reflux for three days under N2. Solvent was then removed under reduced pressure, and the residue was partitioned between CH2Cl2 (100 ml) and 1M Na2CO3 (100 ml). The organic layer was evaporated and the residue chromatographed on alumina, eluting with CH2Cl2 /MeOH (199:1) to give N-[2-(dimethylamino)ethyl]acridine-4-carboxamide (DACA) (1.47 g, 61%), mp (dihydrochloride salt from MeOH/EtOAc) 162-165° C.

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux for three days under N2
  3. customSolvent was then removed under reduced pressure
  4. customthe residue was partitioned between CH2Cl2 (100 ml) and 1M Na2CO3 (100 ml)
  5. customThe organic layer was evaporated
  6. customthe residue chromatographed on alumina
  7. washeluting with CH2Cl2 /MeOH (199:1)

出典と根拠

ORDレコード
ord-1889ca2d54664babbbe07d2030c12d6d
出典データセット
uspto-grants-2000_08
特許番号
US06111109

関連ノート

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