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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 630856Generated: October 31, 2026

Ammonia → HCID 86687145, compound

https://huagongshe.com/reaction/630856

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmoniaHCID 222—
ReactantSodium hydrideHCID 24758—
Reactant(1R,4S)-4-Amino-1,2,3,4-tetrahydronaphthalen-1-olHCID 86686674—
ReactantHCID 86687144HCID 86687144—
SolventMethanolHCID 887—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
SolventDichloromethaneHCID 6344—
ProductHCID 86687145HCID 8668714551.5%

Reaction Conditions

Temperature60 °C

Reaction Steps

To a solution of Intermediate A (161 mg, 0.99 mmol) in dry DMF (2.5 mL) at RT was added NaH (60% in mineral oil, 108 mg, 2.70 mmol) and the mixture stirred for 15 min. Intermediate 91c (214 mg, 0.89 mmol) in DMF (2.5 mL) was then added and the mixture heated at 60° C. for 1 h. After cooling, the resulting dark brown mixture was diluted with water and extracted with DCM. The combined organics were dried and concentrated in vacuo. The residue was purified by FCC, using 0-10% MeOH in DCM, to give crude product. FCC, using 0-10% (2M NH3 in MeOH) in DCM, gave the title compound as light brown foam (175 mg, 51%). LCMS (Method 3): Rt 0.43 min, m/z 382 [MH+].

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09315503B2
Source datasetuspto-grants-2016_04
ORD IDord-4f4af58717d64a6b86a8bcc110a27c4f
Source noteuspto-grants-2016_04