Potassium Carbonate → 2-Aminotetralin

HRID 1656637Notes

Reaction equation

HRID 1656637 reaction equation
C(CO[C:6]1[CH:7]=[CH:8][C:9](OCC2OC2)=[C:10]2[C:15]=1[NH:14][C:13](=O)[CH2:12][CH2:11]2)(=O)C.O[C:23]1C=CC(O)=C2C=1CCC(=O)N2.BrCC(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C.Cl.C1C2C(=CC=CC=2)CCC1NCC(O)COC1C=CC(OCC(=O)C)=C2C=1CCC(=O)N2.O.CC(C)=O>[NH2:14][CH:13]1[CH2:12][CH2:11][C:10]2[C:9](=[CH:8][CH:7]=[CH:6][CH:15]=2)[CH2:23]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11715BromoacetoneHCID 1515652(1H)-Quinolinone, 3,4-dihydro-5,8-dihydroxy-HCID 197883268-Acetylmethoxy-5-(2,3-epoxypropoxy)-3,4-dihydrocarbostyril

Product 1

HCID 346772-Aminotetralin

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 18366337Propan-2-one--water (1/1)SolventHCID 19788260N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(8-acetylmethoxy-3,4-dihydrocarbostyril-5-yloxy)propanamine hydrochlorideSolvent

Procedure

Operating as described in Example 27, but starting from 8-acetylmethoxy-5-(2,3-epoxypropoxy)-3,4-dihydrocarbostyril, prepared by reacting 5,8-dihydroxy-3,4-dihydrocarbostyril with bromoacetone in the presence of potassium carbonate and in a mixture water/acetone 4/1, at the reflux temperature for 5 hours, and 2-aminotetralin (1.48 g) in absolute ethanol (30 ml), N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(8-acetylmethoxy-3,4-dihydrocarbostyril-5-yloxy)propanamine hydrochloride is obtained ((iF): R=H, L"=acetonyloxy, E" and G", taken together, represent a group --CH2 --CH2 --CO--NH--, and the chain is attached to position 2 of the tetralin moiety).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-622a9e10223e4e249d9c9ab9082790f6
Source dataset
uspto-grants-1993_10
Patent number
US05254595

Reaction notes

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