1-Naphthalenemethanamine → HCID 14898709, compound

HRID 1681685Notes

Reaction equation

C(OC(N1C2C(=CC=CC=2)C=CC1OCC)=O)C.[N+:19]([C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([OH:26])=O)([O-:21])=[O:20].C(=O)(OC(=O)C1C=CC=CC=1[N+]([O-])=O)OCC.[C:48]1([CH2:58][NH2:59])[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:51]=[CH:50][CH:49]=1>C(Cl)Cl>[C:48]1([CH2:58][NH:59][C:24](=[O:26])[C:23]2[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=2[N+:19]([O-:21])=[O:20])[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:51]=[CH:50][CH:49]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (7.5 g), was added in portions to a solution of 2-nitrobenzoic acid (5.01 g) in methylene chloride (300 ml) cooled to 0° C. The mixture (containing ethyl 2-nitrobenzoyl carbonate) was stirred for 15 minutes and then 1-naphthylmethylamine (4.7 g) was added dropwise at 0-5° C. The mixture was then stirred for 1 hour at ambient temperature and then washed successively with M hydrochloric acid, M sodium hydroxide and then with water. The organic phase was dried (MgSO4) and evaporated. The residue was purified by column chromatography, eluting with methylene chloride/ether (80/20 v/v) to give N-(1-naphthylmethyl)-2-nitrobenzamide as a white solid (7.9 g), of satisfactory purity.

Workup

stirringThe mixture was then stirred for 1 hour at ambient temperature
washwashed successively with M hydrochloric acid, M sodium hydroxide
dry with materialThe organic phase was dried (MgSO4)
customevaporated
customThe residue was purified by column chromatography
washeluting with methylene chloride/ether (80/20 v/v)

Sources & evidence

ORD record: ord-566007ec702d48dd90fa5e3b5f68fcbc
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05173496

Reaction notes

Loading…