Citric Acid → HCID 178517354, compound

HRID 1017638Notes

Reaction equation

C([Li])CCC.[C:6]([CH2:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11](OC)=[O:12])#[N:7].[C:19]1([N:25]=[N+:26]=[N-:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[C:19]1([N:25]2[C:6]3=[N:7][C:11](=[O:12])[C:10]4[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=4[C:8]3=[N:27][NH:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyllithium (1.6 M, 7.5 ml, 12 mmol) was added dropwise at −78° C. over 5 min to a stirred solution of methyl 2-cyanomethylbenzoate (Tetrahedron Lett., 1991, 32, 4133-4134) (2.10 g, 12 mmol) in dry THF (50 ml) under nitrogen. The deep red solution was stirred at −78° C. for 10 min, followed by the addition of a solution of phenyl azide (1.47 g, 12.3 mmol) in dry THF (10 ml). The green solution was stirred at −78° C. for 1.5 h then warmed to r.t. over 30 min, becoming bright blue. Saturated aqueous ammonium chloride (50 ml) was added and the mixture was acidified to pH 5 with 1M citric acid. The white precipitate was collected and washed with water and diethyl ether, then dried to give 3-phenyl-1,2,3-triazolo[4,5-c]isoquinolin-5-one (2.00 g, 64%). δH (360 MHz; DMSO) 7.58-7.68 (4H, m), 7.80-7.84 (2H, m), 7.93 (1H, ddd, J=8, 8 and 1), 8.30 (2H, d, J=8) and 12.80 (1H, s); m/z (ES+) 263 (M+H+).

Workup

stirringThe green solution was stirred at −78° C. for 1.5 h
temperaturethen warmed to r.t. over 30 min
customThe white precipitate was collected
washwashed with water and diethyl ether
customdried

Sources & evidence

ORD record: ord-b1c8eb70268943c584ac25943102870f
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479506B1

Reaction notes

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