4-Aminobenzonitrile → HCID 178507471, compound

HRID 1678682Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH4+].[Cl-].[N-:12]=[N+:13]=[N-:14].[Na+]>CN(C=O)C>[NH:12]1[C:6]([C:5]2[CH:8]=[CH:9][C:2]([NH2:1])=[CH:3][CH:4]=2)=[N:7][N:14]=[N:13]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a stirred solution of 4-amino-benzonitrile (300 mg, 2.53 mmol; CAS Reg. No. 873-74-5) in dry DMF (6 ml) was added NH4Cl (547 mg, 10.2 mmol) and NaN3 (660 mg, 10.2 mmol) at room temperature. The reaction mixture was then heated at 120° C. for 12 h. After cooling, TLC shows formation of new spot, filtered the solid material by sintered funnel and washed the solid residue by EtOAc (4×5 ml). Combined organic layers were reduced under pressure at 60° C. and diluted the residue with EtOAc (25 mL). Organic layer was washed with H2O (15 ml), brine (12 ml) and dried over Na2SO4; which was then concentrated under reduced pressure to give the crude material (300 mg). Crude product was then purified by column chromatography [SiO2 (230-400 mesh), MeOH:DCM 5:95] to give the title compound (180 mg, 44.4%) as light yellow solid.

Workup

temperatureAfter cooling
filtrationTLC shows formation of new spot, filtered the solid material by sintered funnel
washwashed the solid residue by EtOAc (4×5 ml)
customwere reduced under pressure at 60° C.
additiondiluted the residue with EtOAc (25 mL)
washOrganic layer was washed with H2O (15 ml), brine (12 ml)
dry with materialdried over Na2SO4
concentrationwhich was then concentrated under reduced pressure
customto give the crude material (300 mg)
customCrude product was then purified by column chromatography [SiO2 (230-400 mesh), MeOH:DCM 5:95]

Sources & evidence

ORD record: ord-0de09a0fe74149ea8501ecd89ef15454
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008505B2

Reaction notes

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