6-Methoxy-alpha-tetralone → HCID 9991364, compound

HRID 845071Notes

Reaction equation

HRID 845071 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[CH2:8][CH2:7][CH2:6]2.O.[C:15]([OH:19])(=O)[CH:16]=O.O.[NH2:21][NH2:22]>>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:9]3[C:8](=[CH:16][C:15](=[O:19])[NH:21][N:22]=3)[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

4

Reactant 3

HCID 141126-Methoxy-alpha-tetraloneHCID 24654Hydrazine hydrate (1:1)HCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 9991364HCID 9991364, compound

Procedure

In a manner similar to that described in Preparation 3, 6-methoxy-1-tetralone was treated with glyoxylic acid monohydrate and hydrazine hydrate to give 5,6-dihydro-8-methoxybenzo[h]cinnolin-3[2H]-one (m.p. 246-8°; from aqueous ethanol); ν(Nujol mull) 3320-2200, 1667, 1601, 1270 and 1048 cm-1 ; δ(DMSO-d6) 2.81 (4H,m,5,6-H2), 3.80 (3H,s,OCH3), 6.71 (1H,s,4-H), 6.90 (2H,m,7,9-H), 7.82 (1H,m,10-H), 12.73 (1H,s,NH).

Sources & evidence

ORD record
ord-3f583deca46049878ec00a96a088a525
Source dataset
uspto-grants-1988_07
Patent number
US04755511

Reaction notes

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