HCID 22262102, compound → HCID 45089717, compound

HRID 749480Notes

Reaction equation

HRID 749480 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=1)([O-])=O.[N+](C1C2CCCCC=2C(C(OC)=O)=CC=1)([O-])=O>CO>[NH2:1][C:4]1[CH:5]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=1

Participants

4

Reactant 2

HCID 22262102HCID 22262102, compoundHCID 68980195HCID 68980195, compound

Product 1

HCID 45089717HCID 45089717, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-nitro-5,6,7,8-tetrahydronaphthalene-1-carboxylate (see Zh Obshch Khim; 1948, 877-884; 1.4 g, 3 mmol), which was contaminated with its regioisomer methyl 4-nitro-5,6,7,8-tetrahydronaphthalene-1-carboxylate (1:1), was dissolved in methanol (50 mL). The solution was flushed with nitrogen whereupon Pd/C (5%) catalyst (0.19 g) was added. The mixture was stirred under H2 at room temperature until the consumption of gas ceased. The catalyst was removed by filtration and then the solvent was evaporated. The product was separated from its 4-amino regioisomer and by-products by chromatography on silica gel using CH2Cl2 and triethylamine (98:2). There was obtained 0.24 g (39%) of methyl 3-amino-5,6,7,8-tetrahydronaphthalene-1-carboxylate as an oil. 1H NMR (500 MHz, CDCl3): 1.7-1.8 (m, 4H), 2.7 (m, 2H), 2.9 (m, 2H), 3.8 (s, 3H), 6.6 (d, 1H), 7.0 (d, 1H).

Workup

  1. customThe solution was flushed with nitrogen whereupon Pd/C (5%) catalyst (0.19 g)
  2. additionwas added
  3. customThe catalyst was removed by filtration
  4. customthe solvent was evaporated
  5. customThe product was separated from its 4-amino regioisomer and by-products by chromatography on silica gel

Sources & evidence

ORD record
ord-0c8b31b3c9654281b44ef1bc583478d0
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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