Hydrochloric Acid → HCID 9968022, compound

HRID 1595787Notes

Reaction equation

HRID 1595787 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:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][N:23]=[CH:22]2.Cl.N1C=CC=CC=1.C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+].Cl>O>[NH:24]1[C:25]2[C:21](=[CH: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:27][CH:26]=2)[CH:22]=[N:23]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 880121H-Indazol-5-amineHCID 101298981-EthoxyethanolHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 9968022HCID 9968022, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.249 g of 4-chloro-6,7-dimethoxy-quinolin-3-carbonitrile, 0.132 g of 5-aminoindazole, 0.020 g of pyridine hydrochloride, and 10 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 2 hours. The mixture was cooled and added to 40 ml of water. To this mixture was added sodium carbonate and concentrated hydrochloric acid to adjust pH to 7. The product was collected, washed with water, and dried to give 0.252 g of 4-(1H-indazol-5-ylamino)-6,7-dimethoxy-quinoline-3-carbonitrile as a solid, mp 290-295° C.; mass spectrum (EI, m/e): M 345.1217.

Workup

  1. temperatureat reflux temperature for 2 hours
  2. temperatureThe mixture was cooled
  3. customThe product was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-da4c8042bc7548fc9f5bc36313460888
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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