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

HRID 604610노트

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HRID 604610 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-].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]

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-carbonitrile

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 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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f635a2f3ad364d1e8347fd859c92512c
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910592B2

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