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

HRID 604610ノート

反応式

HRID 604610 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-].C(Cl)Cl>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

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 CH2Cl2 was added and resulting mixture was filtered. The filtrate was partitioned between two layers. The aqueous layer was extracted with CH2Cl2 (1×). The combined organic layers were concentrated in vacuo. The residue was dissolved in Et2O. The Et2O layer was washed with aqueous Na2S2O3, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (Si, hexanes/EtOAc) yielding 6-aminoindane-5-carbonitrile. LCMS calc.=159.1; 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 CH2Cl2 (1×)
  5. concentrationThe combined organic layers were concentrated in vacuo
  6. dissolutionThe residue was dissolved in Et2O
  7. washThe Et2O layer was washed with aqueous Na2S2O3
  8. dry with materialdried (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-f635a2f3ad364d1e8347fd859c92512c
出典データセット
uspto-grants-2011_03
特許番号
US07910592B2

反応ノート

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