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

HRID 537975Notes

Reaction equation

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]

Participants

Conditions

Temperature: 160 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-cefec463b1a147a1b2d858f5bc0d3f5b
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865707B2

Reaction notes

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