Dichloromethane → 6-amino-2,3-dihydro-1H-indene-5-carbonitrile

HRID 537975ノート

反応式

HRID 537975 の反応式
I[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH2:8]2)=[CH:4][C:3]=1[NH2:11].[Cu][C:13]#[N:14].[NH4+].[OH-].ClCCl>CN(C=O)C>[NH2:11][C:3]1[CH:4]=[C:5]2[C:9]([CH2:8][CH2:7][CH2:6]2)=[CH:10][C:2]=1[C:13]#[N:14]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 14923Ammonium HydroxideHCID 224002936-iodo-2,3-dihydro-1H-inden-5-amineHCID 178418546HCID 178418546、化合物

生成物 1

HCID 451221766-amino-2,3-dihydro-1H-indene-5-carbonitrile収率 59%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
160 °C

実験手順

To a solution of 6-iodoindan-5-amine (135 mg, 0.52 mmol) in DMF (2 mL), was added copper (I) cyanide (93 mg, 1.04 mmol). The mixture was heated at 160° C. for 1.5 h. The reaction mixture was poured into 10% NH4OH. An equal amount of dichloromethane was added and resulting mixture was filtered. The filtrate was partitioned between two layers. The aqueous layer was extracted with dichloromethane (1×). The combined organic layers were concentrated in vacuo. The residue was dissolved in ethyl ether. The ether layer was washed with aqueous sodium bisulfite, dried with Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (Si, hexanes/EtOAc) yielding 6-aminoindane-5-carbonitrile (48.5 mg, 59%). LCMS calc.=158.08; found=159.1 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 7.22 (s, 1H), 6.64 (s, 1H), 4.25 (br, s, 2H), 2.85 (t, J=7.4 Hz, 2H), 2.80 (t, J=7.4 Hz, 2H), 2.09-2.03 (m, 2H).

後処理

  1. customresulting mixture
  2. filtrationwas filtered
  3. customThe filtrate was partitioned between two layers
  4. extractionThe aqueous layer was extracted with dichloromethane (1×)
  5. concentrationThe combined organic layers were concentrated in vacuo
  6. dissolutionThe residue was dissolved in ethyl ether
  7. washThe ether layer was washed with aqueous sodium bisulfite
  8. dry with materialdried with Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography (Si, hexanes/EtOAc)

出典と根拠

ORDレコード
ord-cefec463b1a147a1b2d858f5bc0d3f5b
出典データセット
uspto-grants-2014_10
特許番号
US08865707B2

反応ノート

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