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

HRID 537975노트

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HRID 537975 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
160 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-cefec463b1a147a1b2d858f5bc0d3f5b
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865707B2

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