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

HRID 604610Notes

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-].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]

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 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).

Workup

customresulting mixture
filtrationwas filtered
customThe filtrate was partitioned between two layers
extractionThe aqueous layer was extracted with CH2Cl2 (1×)
concentrationThe combined organic layers were concentrated in vacuo
dissolutionThe residue was dissolved in Et2O
washThe Et2O layer was washed with aqueous Na2S2O3
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (Si, hexanes/EtOAc)

Sources & evidence

ORD record: ord-f635a2f3ad364d1e8347fd859c92512c
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910592B2

Reaction notes

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