Hydrazine hydrate (1:1) → HCID 135707805, compound

HRID 845063Notes

Reaction equation

HRID 845063 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH2:7][CH2:6][CH2:5]2.O.[C:14]([OH:18])(=O)[CH:15]=O.O.[NH2:20][NH2:21]>>[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]3[C:7](=[CH:15][C:14](=[O:18])[NH:20][N:21]=3)[CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenoneHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 135707805HCID 135707805, compound

Procedure

In a manner similar to that given in Preparation 3, 6-hydroxy-1-tetralone was treated with glyoxylic acid monohydrate and hydrazine hydrate to give 5,6-dihydro-8-hydroxybenzo[h]cinnolin-3[2H]-one (m.p. 300°, from dimethylformamide/ethanol); ν(Nujol mull) 3400-2000, 1652, 1594, and 1582cm-1 ; δ(DMSO-d6) 2.77 (4H,s,5,6-H2), 6.65 (2H,m, 4,7-H), 6.74 (1H,m,9-H), 7.73 (1H,d,10-H), 9.93 (1H,d(br),OH), 12.7 (1H,d(br)NH).

Sources & evidence

ORD record
ord-06980480a7d144d9bd700695d9fe5c0b
Source dataset
uspto-grants-1988_07
Patent number
US04755511

Reaction notes

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