5-Tetralinylamine → HCID 21704832, compound

HRID 1595800Notes

Reaction equation

HRID 1595800 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[C:28]2[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=2[CH:22]=[CH:21][CH:20]=1.Cl.N1C=CC=CC=1>C(OCCO)C>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][C:3]([C:16]#[N:17])=[C:2]2[NH:18][C:19]1[C:28]2[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=2[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 166715-TetralinylamineHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 21704832HCID 21704832, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

Using an analogous procedure to that described in Example 150, 248.7 mg (1 mmol) of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile, 176.7 mg (1.2 mmol) of 1-amino-5,6,7,8-tetrahydronaphthalene and 115.6 mg (1 mmol) of pyridine hydrochloride in 12 mL of 2-ethoxyethanol was refluxed for 2 hr. The work up gave 195.1 mg (54.3%) of the product as a yellow solid, m.p. 248° C. (dec.), mass (electrospray, m/e): M+H 360.1. HRCIMS: calcd 359.163 for C22H16N3O2Cl(M+), obsd 359.1632.

Workup

  1. temperaturewas refluxed for 2 hr

Sources & evidence

ORD record
ord-d137c9128f3c4b7cbbbf5f560182cb92
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

Loading…