Methylamine → HCID 18790639, compound

HRID 1075517Notes

Reaction equation

HRID 1075517 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]([OH:14])=O)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[CH3:15][NH2:16]>O1CCCC1>[CH3:15][NH:16][C:12](=[O:14])[CH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[C:2](=[O:1])[CH2:3][CH2:4]2

Participants

4

Reactant 2

HCID 6329MethylamineHCID 10241615(1-Oxo-2,3-dihydro-1H-inden-5-yl)acetic acid

Product 1

HCID 18790639HCID 18790639, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-Methyl(1-oxoindan-5-yl)acetamide can be obtained in the following way: 16 g of N,N'-carbonyldiimidazole are added portionwise to a solution of 12.5 g of (1-oxoindan-5-yl)acetic acid in 250 ml of tetrahydrofuran maintained at 0° C. After reacting for 1 hour at a temperature in the region of 20° C., the solution is cooled to -10° C. and a stream of monomethylamine is passed into the mixture for 5 minutes. After returning to a temperature in the region of 20° C., the reaction mixture is evaporated under reduced pressure. The residue is taken up in 1 liter of dichloromethane. The organic phase is washed three times with 500 ml of distilled water, dried over magnesium sulphate and then evaporated. The resulting brown solid is purified by flash chromatography on silica (eluent dichloromethane/methanol (96/4 by volume)). 9 g of N-methyl(1-oxoindan-5-yl)acetamide are thus obtained in the form of a white solid melting at 169° C. (1H NMR spectrum in CDCl3, T=300K, δ in ppm: 2.69 (2H, m, COCH2), 2.80 (3H, d, NCH3), 3.14 (2H, t, J=5 Hz, CH2), 3.65 (2H, s, CH2), 5.47 (1H, broad s, NH), 7.26 (1H, d, J=7 Hz, arom. CH), 7.42 (1H, s, arom. CH), 7.74 (1H, d, J=7 Hz, arom. CH)).

Workup

  1. temperaturethe solution is cooled to -10° C.
  2. customAfter returning to a temperature in the region of 20° C.
  3. customthe reaction mixture is evaporated under reduced pressure
  4. washThe organic phase is washed three times with 500 ml of distilled water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe resulting brown solid is purified by flash chromatography on silica (eluent dichloromethane/methanol (96/4 by volume))

Sources & evidence

ORD record
ord-9900ae72f6ac4ec28459bfa32260dfbc
Source dataset
uspto-grants-1999_05
Patent number
US05902803

Reaction notes

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