Hydrochloric Acid → 6-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 968651ノート

反応式

HRID 968651 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=O)[CH2:6][CH2:5]2.[BH3-]C#[N:15].[Na+].Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([NH2:15])[CH2:6][CH2:5]2

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 27335536-Bromo-2-tetraloneHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 100595666-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine収率 276.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

This material is commercially available, however, it can be successfully prepared by the following procedure. To a solution of the 6-bromo 2-tetralone (0.288 g, 1.280 mmol) and NH4OAc (0.986 g, 10 eq.) in MeOH (40 mL) is added NaCNBH3 (0.097 g, 1.2 eq) at room temperature. The resulting yellow solution is stirred at that temperature for 20 hours, then acidified with 0.1 M HCl to pH 2.0. The mixture is extracted with CH2Cl2 twice. The aqueous layer is basified with 1.0 N NaOH to pH 10 then extracted with CH2Cl2 three times. The extracts are dried over anhydrous MgSO4 and concentrated in vacuo to afford 0.8 g (44% yield) of the desired product as a yellow oil which is used without further purification. 1H NMR (300 MHz, CD3OD) δ 7.27-7.35 (m, 8H), 7.05 (d, J=8.4 Hz, 4H), 3.56 (m, 1H), 3.17 (dd, J=3.9, 16.2 Hz, 1H), 2.95 (m, 2H), 2.81 (dd, J=9.9, 16.2 Hz, 1H), 2.19-2.29 (m, 1H), 1.79-1.92 (m, 1H); 13C NMR (75 MHz, CD3OD) δ 137.3, 131.5, 131.4, 130.9, 120.1, 47.4, 26.9, 26.7; LRMS: 226.1 (M+H), 209 (M+H−NH3).

後処理

  1. customhowever, it can be successfully prepared by the following procedure
  2. extractionThe mixture is extracted with CH2Cl2 twice
  3. extractionthen extracted with CH2Cl2 three times
  4. dry with materialThe extracts are dried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-de25e0a6c07f49faba21e3d937e55164
出典データセット
uspto-grants-2007_12
特許番号
US07304065B2

反応ノート

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