Sodium Carbonate → HCID 9924834, compound

HRID 1595783Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[NH2:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH:21]=[CH:22][N:23]=[CH:24]2.Cl.N1C=CC=CC=1.C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH:24]1[C:25]2[C:20](=[C:19]([NH:18][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][C:3]=3[C:16]#[N:17])[CH:28]=[CH:27][CH:26]=2)[CH:21]=[CH:22][N:23]=1

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 0.249 g of 4-chloro-6,7-dimethoxy-quinolin-3-carbonitrile, 0.288 g of 5-aminoisoquinoline, 0.020 g of pyridine hydrochloride, and 10 ml of ethoxyethanol was heated under nitrogen in a sealed tube at 200° C. for 2 hours. The mixture was cooled and added to 100 ml of water. To this mixture was added sodium carbonate to pH 9. The product was collected, washed with water, and dried to give 0.100 g of 4-(isoquinolin-5-ylamino)-6,7-dimethoxy-quinoline-3-carbonitrile as a solid, mp 140° C. (decomposed); mass spectrum (EI, m/e): M 356.1279.

Workup

temperatureThe mixture was cooled
customThe product was collected
washwashed with water
customdried

Sources & evidence

ORD record: ord-337a24f86d45414cab90c8d406e52453
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288082B1

Reaction notes

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