Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1) → HCID 22462802, compound

HRID 1936838Notes

Reaction equation

HRID 1936838 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=O)=[CH:4][CH:3]=1.Cl.[NH:13]([C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18])N>C(O)C.O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3[C:23]4[C:15](=[C:16]([C:17]([OH:19])=[O:18])[CH:20]=[CH:21][CH:22]=4)[NH:13][C:8]=32)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 104169Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1)HCID 1397781-Indanone, 6-bromo-

Product 1

HCID 22462802HCID 22462802, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-bromoindanone (0.447 g, 2.12 mmol) [Adamczyk, M. et al. J. Org. Chem. 1984, 49, 4226-4237] in ethanol (100 mL) was added a solution of 2-hydrazinobenzoic acid hydrochloride (0.800 g, 4.24 mmol) in deionized water (50 mL). The mixture was stirred for 1 h then cooled to 0° C. The precipitated hydrazone was vacuum filtered and dried in vacuo to afford 0.628 g (86%) of the title compound as a yellow solid: mp 186° C. (dec).

Workup

  1. filtrationfiltered
  2. customdried in vacuo

Sources & evidence

ORD record
ord-2d85442d148d49f1a587050732216404
Source dataset
uspto-grants-2002_05
Patent number
US06391902B1

Reaction notes

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