Acetic Acid → HCID 15871447, compound

HRID 1953539Notes

Reaction equation

HRID 1953539 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][C:10](=O)[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.C1COCC1>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]([NH:22][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 113214437-Nitro-2-tetralone

Product 1

HCID 15871447HCID 15871447, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

7-Nitro-3,4-dihydro-2(1H)-naphthaleneone (1.50 g, 7.85 mmol), benzylamine (430 ml, 39.3 mmol), acetic acid (8.0 ml), 4 Å molecular sieves (20 ml), THF (15 ml), and MeOH (15 ml) were introduced into a flask and cooled to 0° C. Sodium cyanoborohydride (0.99 g, 15.7 mmol) was then added portionwise over a 5-minute period. The mixture was stirred for 14 hr, filtered through celite, and concentrated to a syrup. The mixture was made basic with 2N NaOH and extracted with ether (3×50 ml). The combined extracts were washed with water, dried over magnesium sulfate, filtered, concentrated and chromatographed over silica gel (3% methanol/methylene chloride) to yield 7-nitro-2-((phenylmethyl)amino)-1,2,3,4-tetrahydronaphthalene: (2.10 g, 95%); M.S. (M+H)+ =283.

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated to a syrup
  3. extractionextracted with ether (3×50 ml)
  4. washThe combined extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed over silica gel (3% methanol/methylene chloride)

Sources & evidence

ORD record
ord-c7917d4494614a04a7effb4c97c0d824
Source dataset
uspto-grants-2000_09
Patent number
US06117898

Reaction notes

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