3-Anilinopropionitrile → (RS)-3-Anilino-2-(2-cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-yl-methyl)acrylonitrile

HRID 964973Notes

Reaction equation

[CH:1]1([CH:4]2[CH:9]=[CH:8][C:7]3=[C:10]([CH:18]=O)[CH:11]=[C:12]([O:16][CH3:17])[C:13]([O:14][CH3:15])=[C:6]3[O:5]2)[CH2:3][CH2:2]1.[NH:20]([CH2:27][CH2:28][C:29]#[N:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CS(C)=O>[NH:20]([CH:27]=[C:28]([CH2:18][C:10]1[C:7]2[CH:8]=[CH:9][CH:4]([CH:1]3[CH2:2][CH2:3]3)[O:5][C:6]=2[C:13]([O:14][CH3:15])=[C:12]([O:16][CH3:17])[CH:11]=1)[C:29]#[N:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 10 °C

Procedure

30 g of (RS)-2-cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-carbaldehyde and 17.5 g of 3-anilinopropionitrile were dissolved in 300 ml of dimethyl sulphoxide under argon, cooled to 10° C. and treated portionwise with 13.5 g of potassium tert.butylate. Subsequently, the mixture was stirred at 10° C. for a further 1 hr. and at 20° C. for 5 hrs. For the working up, the mixture was poured on to 3 l of ice/water and extracted: 2×3 l of ethyl acetate, 2×3 l of water. The crude product was purified by silica gel chromatography with hexane/ethyl acetate 5:1 to 2:1 and crystallized from hexane/ethyl acetate. (RS)-3-Anilino-2-(2-cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-yl-methyl)acrylonitrile was obtained as white crystals, m.p. 140° C.

Workup

waitand at 20° C. for 5 hrs
extractionextracted
customThe crude product was purified by silica gel chromatography with hexane/ethyl acetate 5:1 to 2:1
customcrystallized from hexane/ethyl acetate

Sources & evidence

ORD record: ord-86da13a9c2e04ddab4b5301cba3d6c80
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05773446

Reaction notes

Loading…