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Acetic Acid → [2-(3,4-Dihydro-1H-isoquinolin-2-yl)ethyl]-(7-nitro-1,2,3,4-tetrahydro-naphthalen-1-yl)amine

HRID 914992
Notes
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Reaction equation

HRID 914992 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][CH2:12][N:13]=[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=2)[CH2:17][CH2:16][CH2:15]1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][CH2:12][NH:13][CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=2)[CH2:17][CH2:16][CH2:15]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 58958206[2-(3,4-Dihydro-1H-isoquinolin-2-yl)ethyl]-(7-nitro-3,4-dihydro-2H-naphthalen-1-ylidene)amine

Product 1

HCID 58958235[2-(3,4-Dihydro-1H-isoquinolin-2-yl)ethyl]-(7-nitro-1,2,3,4-tetrahydro-naphthalen-1-yl)amineYield 53%

Reagents, catalysts & solvents 1

HCID 6365
1,1-Dichloroethane
Solvent

Procedure

To a solution of 96 (1.42 g, 4.07 mmol) in anhydrous dichloroethane (10 mL) were sequentially added acetic acid (267 mg, 4.48 mmol) and NaBH(OAc)3 (1.12 g, 5.29 mmol) under N2. The reaction was stirred at room temperature for 2 hours before it was quenched by slow addition of water (100 mL). The mixture was extracted with dichloromethane (100 mL) and the organic layer was sequentially washed with water (100 mL), saturated aq. NaHCO3 (100 mL), and water (100 mL). The residue, from drying (Na2SO4) and concentrating the organic layer, was chromatographed on silica gel (EtOAc to 5:1 EtOAc/CH3OH) to yield 97 as a brown oil (755 mg, 53%).

Workup

  1. customwas quenched by slow addition of water (100 mL)
  2. extractionThe mixture was extracted with dichloromethane (100 mL)
  3. washthe organic layer was sequentially washed with water (100 mL), saturated aq. NaHCO3 (100 mL), and water (100 mL)
  4. dry with materialThe residue, from drying (Na2SO4)
  5. concentrationconcentrating the organic layer
  6. customwas chromatographed on silica gel (EtOAc to 5:1 EtOAc/CH3OH)

Sources & evidence

ORD record
ord-975ab0393c2142cd90033175a94dbf65
Source dataset
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07265122B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes