4-Chloronaphthylamine → HCID 23514381, 화합물

HRID 353600

반응식

HRID 353600 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

HCID 23514381HCID 23514381, 화합물수율 2,089.2%

시약·촉매·용매 3

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 887Methanol용매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ab9d87d4ffa14605a878d926f1c8b7cb
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06753429B2

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