Triethylamine → (+)-trans-1-(3,4-Dichlorobenzamido)-2-hydroxy-7-nitrotetraline

HRID 1937360Notes

Reaction equation

HRID 1937360 reaction equation
[NH2:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[CH2:5][CH2:4][C@H:3]1[OH:15].C(N(CC)CC)C.[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[Cl:33])[C:27](Cl)=[O:28]>C1COCC1>[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[Cl:33])[C:27]([NH:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[CH2:5][CH2:4][C@H:3]1[OH:15])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 21338530(+)-trans-1-Amino-2-hydroxy-7-nitrotetraline

Product 1

HCID 21338528(+)-trans-1-(3,4-Dichlorobenzamido)-2-hydroxy-7-nitrotetralineYield 103.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 112 (2.1 g) in warm THF (300 mL) was treated with triethylamine (5 mL) and the solution allowed to come to room temperature. A solution of 3,4-dichlorobenzoyl chloride (2.3 g) in THF (50 mL) was added dropwise over 20 min. After stirring over night, the solvent was evaporated to give a solid (3.97 g) that had the appropriate nmr spectrum.

Workup

  1. customto come to room temperature
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-102accdd4c434bc1a1a09fe58fb623ef
Source dataset
uspto-grants-2002_05
Patent number
US06395735B2

Reaction notes

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