1-Tetralone → Benzo(h)cinnolin-3(2H)-one, 5,6-dihydro-

HRID 845070Notes

Reaction equation

HRID 845070 reaction equation
[C:1]1(=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.O.[C:13]([OH:17])(=O)[CH:14]=O.O.[NH2:19][NH2:20]>>[N:19]1[NH:20][C:13](=[O:17])[CH:14]=[C:2]2[C:1]=1[C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:4][CH2:3]2

Participants

4

Reactant 3

HCID 107241-TetraloneHCID 24654Hydrazine hydrate (1:1)HCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 213230Benzo(h)cinnolin-3(2H)-one, 5,6-dihydro-

Procedure

In a manner similar to that described in Preparation 3, 1-tetralone was treated with glyoxylic acid monohydrate and hydrazine hydrate to give 5,6-dihydrobenzo[h]cinnolin- 3[2H]-one (m.p. 260-1°; from ethanol) ν(Nujol mull) 3350-2200, 1665, 1610 and 1600 cm-1 ; δ(DMSO-d6) 2.88 (4H,s,5,6-H2), 6.77 (1H,s,4-H), approx 7.3 (3H,m,7,8,9-H), 7.92 (1H,m,10-H), 12.9 (1H,br,NH).

Sources & evidence

ORD record
ord-6e50112f730840db8c481c0dacf75bc2
Source dataset
uspto-grants-1988_07
Patent number
US04755511

Reaction notes

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