Water → HCID 13191334, compound

HRID 1733316Notes

Reaction equation

HRID 1733316 reaction equation
O.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH3:13].Br[CH:15]1[CH2:20][CH2:19][O:18][C:16]1=[O:17].CC1C=CC=C(C)N=1>CC(C)=O>[CH3:13][C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[NH:2][CH:20]1[CH2:19][O:18][C:16](=[O:17])[CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 167332-Methyl-1-naphthylamineHCID 954632(3H)-Furanone, 3-bromodihydro-

Product 1

HCID 13191334HCID 13191334, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 200-ml round-bottom flask equipped with a heating mantle and connected to a water aspirator vacuum system was charged with 15.0 g (0.1 mol) 1-amino-2-methylnaphthalene, 16.4 g (0.1 mol) alpha-bromo-gamma-butyrolactone and 10.7 g (0.1 mol) 2,6-dimethylpyridine. The reaction mixture was maintained at about 94°-101° C. and 160 mm of Hg for about 7 hours. The reaction mixture was cooled, diluted with 100 ml acetone and filtered. The filtrate was evaporated under reduced pressure to give an oily residue which was eluted through a silica gel column with 15% acetone/85% petroleum ether to give 14.6 g of 3-(N-2-methylnaphth-1-ylamino)-gamma-butyrolactone, m.p. 92°-94° C. Elemental analysis for C15H15NO2 showed: %C, calc. 75.0, found 74.5; %H, calc. 5.9, found 5.6; %N, calc. 5.8, found 5.6.

Workup

  1. customA 200-ml round-bottom flask equipped with a heating mantle
  2. temperatureThe reaction mixture was maintained at about 94°-101° C.
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure
  6. customto give an oily residue which
  7. washwas eluted through a silica gel column with 15% acetone/85% petroleum ether

Sources & evidence

ORD record
ord-16a7b53de7b7413e96bea1963e7372e2
Source dataset
uspto-grants-1980_12
Patent number
US04241078

Reaction notes

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