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

HRID 650446

反応式

HRID 650446 の反応式
[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]

参加物

7

反応物 4

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 22728543Water ethylacetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1db6f5db138e4451874059b5298811ea
出典データセット
uspto-grants-2001_08
特許番号
US06274119B1

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