2-Bromoethanol → 3-Amino-4-chloro-5-((2-hydroxyethyl)amino)benzonitrile

HRID 921863Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([NH2:11])[C:9]=1[Cl:10])[C:5]#[N:6].CCN(C(C)C)C(C)C.Br[CH2:22][CH2:23][OH:24]>CN(C=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([NH:11][CH2:22][CH2:23][OH:24])[C:9]=1[Cl:10])[C:5]#[N:6]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3,5-diamino-4-chlorobenzonitrile (200 mg, 1.193 mmol) in DMF (2 mL) was added Hunig's base (2.501 mL, 14.32 mmol) followed by 2-bromoethanol (0.506 mL, 7.16 mmol). The resulting solution was heated at 100° C. for 10 h. LC-MS indicated ca. 30% conversion. It was passed through a pad of celite, rinsed with EtOAc. After concentration, purification via silica gel chromatography (0-70% EtOAc in Hexanes, 24 g) gave 3-amino-4-chloro-5-((2-hydroxyethyl)amino)benzonitrile (75 mg) as an orange oil.

Workup

washrinsed with EtOAc
concentrationAfter concentration, purification via silica gel chromatography (0-70% EtOAc in Hexanes, 24 g)

Sources & evidence

ORD record: ord-63a705d22e104097ae9b8962701f038b
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273057B2

Reaction notes

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