Hydrochloric Acid → HCID 19748915, compound

HRID 1031927Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][N:14]=1.C(N(CC)[C:26](=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[N:29][C:28]=1[CH3:33])C.[ClH:37].[NH4+].[OH-]>O1CCCC1.O>[ClH:37].[CH:21]1[C:22]2[CH:13]3[N:14]([C:26](=[O:34])[C:27]4[CH:32]=[CH:31][CH:30]=[N:29][C:28]=4[CH2:33]3)[CH2:15][CH2:16][C:17]=2[CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: -20 °C

Procedure

Diisopropylamine (28 ml) and 150 ml of tetrahydrofuran were cooled to -65° C. and 125 mL of 1.6M n-butyllithium was added. To the resulting solution was added a solution of 16.2 g of 3,4-dihydroisoquinoline and 38.4 g of 2-methylnicotinic acid diethylamide in tetrahydrofuran. The mixture was allowed to warm to -20° C. and 600 ml of 3N hydrochloric acid was then added followed by 200 ml of water. The mixture was basified with NH4OH and extracted twice with ether. The ether extracts were combined, dried over anhydrous magnesium sulfate and evaporated to a residue, which was dissolved in methanol and acidified with anhydrous HCl in ether. Acetone (50 ml) was added and the mixture was allowed to stand overnight. The crystalline product was collected by filtration, yielding 34 g of (±) 5,6,13,13a-tetrahydroisoquino[2,1-g][1,6]naphthyridine-8-one hydrochloride, m.p. 220°-222° C.

Workup

extractionextracted twice with ether
dry with materialdried over anhydrous magnesium sulfate
customevaporated to a residue, which
dissolutionwas dissolved in methanol
additionAcetone (50 ml) was added
filtrationThe crystalline product was collected by filtration

Sources & evidence

ORD record: ord-d24b765160214976ba4d72cbd01c52d0
Source dataset: uspto-grants-1990_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04956365

Reaction notes

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