2,2-Diethoxyacetaldehyde → 8-Bromoisoquinolin-1(2H)-one

HRID 1782003Notes

Reaction equation

HRID 1782003 reaction equation
C(OC([O:7][CH2:8][CH3:9])C=O)C.[Br:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2C=1C=[N:18][CH:17]=[CH:16]2>>[Br:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:9]=1[C:8](=[O:7])[NH:18][CH:17]=[CH:16]2

Participants

3

Reactant 2

HCID 2196092,2-DiethoxyacetaldehydeHCID 98591348-Bromoisoquinoline

Product 1

HCID 529877478-Bromoisoquinolin-1(2H)-one

Procedure

The isoquinolin-8-yl system can be prepared from the appropriately substituted benzylamine by cyclocondensation with diethoxy-acetaldehyde (see, for example, K. Kido and Y. Watanabe, Chemical & Pharmaceutical Bulletin, 35(12), 4964-6; 1987). Alternatively 8-bromo-isoquinoline (prepared by the method of F. T. Tyson, J.A.C.S., 1939, 61, N. Briet et al., Tetrahedron (2002), 58(29), 5761-5766 or W. D. Brown, et al., Synthesis (2002), (1), 83-86. 183 can be subjected to N-oxidation and rearrangement to give 8-bromo-2H-isoquinolin-1-one. This can be N-methylated to give 8-bromo-2-methyl-2H-isoquinolin-1-one, an appropriate intermediate for the 2-methyl-1-oxo-1,2-dihydroisoquinolin-8-yl system.

Workup

  1. customBrown, et al., Synthesis (2002), (1), 83-86

Sources & evidence

ORD record
ord-06b6e82898044d80ac59438df31c00cd
Source dataset
uspto-grants-2009_03
Patent number
US07498326B2

Reaction notes

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