Ethyl Acetate → 2-Amino-3-chloro-5-(2,4-dichloro-phenyl)-isonicotinonitrile

HRID 420509Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:7]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[CH:8][N:9]=1)[C:5]#[N:6].C1C(=O)N([Cl:25])C(=O)C1.CCOC(C)=O>CN(C=O)C>[NH2:1][C:2]1[C:3]([Cl:25])=[C:4]([C:7]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[CH:8][N:9]=1)[C:5]#[N:6]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-amino-5-(2,4-dichloro-phenyl)-isonicotinonitrile (300 mg, 1.14 mmol, prepared according to Example 15, Step 6.1) and NCS (159 mg, 1.19 mmol) in DMF (4 mL) was stirred and heated at 50° C. for 3 h. The reaction mixture was cooled to RT, poured into AcOEt (40 mL) and washed with water (10 mL). The organic layer was dried over Na2SO4, filtered and evaporated. The residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, hexane/TBME 95:5→100% TBME) to yield the title compound (310 mg, 0.99 mmol, 87%) as a yellow solid. MS: 296 [M−1]+; HPLC: AtRet=2.43; TLC: RF 0.33 (hexane/TBME 1:1).

Workup

temperatureThe reaction mixture was cooled to RT
washwashed with water (10 mL)
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
customevaporated
customThe residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, hexane/TBME 95:5→100% TBME)

Sources & evidence

ORD record: ord-3e2ea4f74dac44bba80ed902428b7a96
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097617B2

Reaction notes

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