Stannous chloride dihydrate → HCID 67271016, compound

HRID 1696490Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([NH2:16])[CH:7]=1)[CH3:2].[N:18]([O-])=O.[Na+].O.O.[Cl:24][Sn]Cl>Cl>[ClH:24].[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([NH:16][NH2:18])[CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of (3-aminonaphthalen-1-yl)acetic acid ethyl ester (2.7 g, 11.8 mmol) in conc. HCl (20 mL) was added an aqueous solution of NaNO2 (0.9 g, 13 mmol) dropwise at 0-5° C. The resulting mixture was stirred at 0° C. for 30 min and then treated with a solution of SnCl2.2H2O (5.9 g, 26.2 mmol) in conc. HCl at such a rate that the reaction temperature never rose above 5° C. After the addition was completed, the mixture was stirred for another 2 h at RT. The precipitate was collected by filtration and washed with ethyl ether to afford (3-hydrazinonaphthalen-1-yl)-acetic acid ethyl ester hydrochloride as a brown solid (2.3 g, 80% yield).

Workup

additionAfter the addition
stirringthe mixture was stirred for another 2 h at RT
filtrationThe precipitate was collected by filtration
washwashed with ethyl ether

Sources & evidence

ORD record: ord-0da0678078694c2eb5760c60e0e7d6f2
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163756B2

Reaction notes

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