4-Chloronaphthylamine → HCID 23514381、化合物

HRID 1296850

反応式

HRID 1296850 の反応式
[CH2:1]([N:3]([CH2:15][CH3:16])[CH2:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)[CH3:2].[NH2:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([Cl:28])=[CH:20][CH:19]=1.[BH4-].[Na+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1.CO>[Cl:28][C:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18]([NH:17][CH2:11][C:10]2[CH:13]=[CH:14][C:7]([O:6][CH2:5][CH2:4][N:3]([CH2:15][CH3:16])[CH2:1][CH3:2])=[CH:8][CH:9]=2)=[CH:19][CH:20]=1

参加物

7

反応物 3

HCID 784084-ChloronaphthylamineHCID 4116744-(2-(Diethylamino)-Ethoxy)-BenzaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 23514381HCID 23514381、化合物収率 2,089.2%

試薬・触媒・溶媒 3

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 887Methanol溶媒HCID 1140Toluene溶媒

実験手順

A stirred solution of 0.2 gram (0.0001 mole) of 4-(2-(diethylamino)ethoxy)benzaldehyde (prepared in the manner of Step A, Example 3), 0.22 gram (0.0001 mole) of 1-amino-4-chloronaphthalene (available from Aldrich Chemical Company), and one drop of p-toluenesulfonic acid monohydrate (available from Aldrich Chemical Company) in 5 mL of toluene was heated at reflux for ten hours. At the conclusion of this period, the reaction mixture was concentrated under reduced pressure, yielding a residue. The residue was taken up in 5 mL of methanol and about 0.2 grams (0.004 mole) of sodium borohydride was added. The resulting mixture was stirred at ambient temperature for about 18 hours. After this time, the mixture was quenched with water and extracted with several portions of diethyl ether. The extracts were combined, dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 0.8 gram of Compound 84. The NMR spectrum was consistent with the proposed structure.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for ten hours
  3. concentrationAt the conclusion of this period, the reaction mixture was concentrated under reduced pressure
  4. customyielding a residue
  5. customAfter this time, the mixture was quenched with water
  6. extractionextracted with several portions of diethyl ether
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-75cb64f9bedf4ead93f4feb3873e1e84
出典データセット
uspto-grants-2007_07
特許番号
US07247756B2

関連ノート

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