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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 969684Generated: October 30, 2026

Anthranilic Acid → 7-(2-amino-benzoylamino)-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

https://huagongshe.com/reaction/969684

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAnthranilic AcidHCID 227—
ReactantDiisopropylethylamineHCID 81531—
ReactantO-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2733207—
ReactantTert-butyl 7-amino-4,4-dimethyl-3,4-dihydroisoquinoline-2(1H)-carboxylateHCID 21959561—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
Product7-(2-amino-benzoylamino)-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl esterHCID 69510706—

Reaction Conditions

Temperature50 °C

Reaction Steps

A mixture of 7-amino-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (4.0 g, 14.60 mmol), 2-amino-benzoic acid (2.0 g, 14.60 mmol), TBTU (5.2 g, 16.06 mmol) and DIEA (2.7 mL, 16.06 mmol) in DMF (5 mL) was heated (50° C.) for 12 h in a sealed tube. The mixture was diluted with EtOAc and water. The aqueous layer extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (SiO2, 20% EtOAc/hexane) to afford a pinkish solid. MS (ES+): 396.0 (M+H)+. Calc'd for C23H29N3O3-395.49.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07307088B2
Source datasetuspto-grants-2007_12
ORD IDord-f0d1372ae2ee4a8789358b29cb2b028b
Source noteuspto-grants-2007_12