Dimethylamine → 1-(6-(Dimethylamino)naphthalen-2-yl)ethanone

HRID 650446

반응식

HRID 650446 반응식
[CH3:1][NH:2][CH3:3].CN(C)P(=O)(N(C)C)N(C)C.C1(C)C=CC=CC=1.[C:22]([C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30]([O:35][CH3:36])[CH:31]=2)[CH:26]=1)(=[O:24])[CH3:23]>O.C(OCC)(=O)C>[C:22]([C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30]([O:35][CH3:36])[CH:31]=2)[CH:26]=1)(=[O:24])[CH3:23].[C:22]([C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30]([N:2]([CH3:3])[CH3:1])[CH:31]=2)[CH:26]=1)(=[O:24])[CH3:23]

참가 물질

7

반응물 4

HCID 674DimethylamineHCID 1140TolueneHCID 12679HexamethylphosphoramideHCID 775062-Acetyl-6-methoxynaphthalene

생성물 2

HCID 775062-Acetyl-6-methoxynaphthaleneHCID 153339701-(6-(Dimethylamino)naphthalen-2-yl)ethanone수율 123.8%

시약·촉매·용매 1

HCID 22728543Water ethylacetate용매

실험 절차

To a solution of 5.26 g (117 mmol) of dimethylamine in 29 mL of freshly distilled hexamethylphosphoric triamide (HMPT) were added 31 mL of dry toluene and 780 mg (112 mmol) of Li in small pieces. The mixture was stirred under argon at room temperature for 1.5 hours. 2-Acetyl-6-methoxynaphthalene was prepared as described in Arsenijevic et al., Org. Synth. Coll. 1988, 6:34-36, the disclosure of which is incorporated herein by reference. 2-Acetyl-6-methoxynaphthalene (5.57 g, 27.8 mmol) was added in one portion, and stirring was continued for 20 hours. The mixture was cooled in an ice-water bath and poured into a cold water/ethyl acetate mixture (300 mL each). After thorough mixing, the layers were separated, and the water layer was extracted twice with 225 mL of ethyl acetate. Organic extracts were combined, dried, and evaporated to give a yellow solid. Recrystallization from ethanol afforded 3.67 g (64%) of 2-acetyl-6-(dimethylamino)naphthalene (ADMAN) as a yellow solid, melting at 153.5-155° C.: 1H NMR (CDCl3, TMS) δ2.67 (s, 3H, COCH3), 3.15 (s, 6H, N(CH3)2), 6.87 (d, 1H, H-5), 7.17 (dd, 1H, H-7), 7.63 (d, 1H, H-4), 7.80 (d, 1H, H-8), 7.92 (dd, 1H, H-3), 8.32 (bs, 1H, H-1). J1,3=2.3 Hz, J5,7=2.4 Hz, J7,8=9.3 Hz. MS (M+) 213: found: 213. Anal. Calcd for C4H15NO: C, 78.84: H, 7.09; N, 6.57. Found C, 78.96; H, 7.10; N, 6.45.

후처리

  1. stirringstirring
  2. waitwas continued for 20 hours
  3. temperatureThe mixture was cooled in an ice-water bath
  4. customAfter thorough mixing, the layers were separated
  5. extractionthe water layer was extracted twice with 225 mL of ethyl acetate
  6. customdried
  7. customevaporated
  8. customto give a yellow solid
  9. customRecrystallization from ethanol

출처 및 근거

ORD 기록
ord-1db6f5db138e4451874059b5298811ea
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06274119B1

연결된 노트

불러오는 중…