Methylamine → N-methyl-2,3-dihydro-1H-indene-1-carboxamide

HRID 1032265

Reaction equation

HRID 1032265 reaction equation
[CH3:1][NH2:2].[CH:3]1([C:12](Cl)=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1>C(OCC)(=O)C>[CH3:1][NH:2][C:12]([CH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)=[O:13]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 13953782HCID 13953782, compound

Product 1

HCID 14822650N-methyl-2,3-dihydro-1H-indene-1-carboxamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 150 ml of ethyl acetate and 50 ml of 40% aqueous methylamine (approx. 0.5M) was stirred in an ice bath, while a solution of 11.7 g (65 mmol) of indane-1-carboxylic acid chloride, a compound of Formula 4 prepared, for example, as described in Preparation 4, dissolved 40 ml of ethyl acetate was added over a period of 15 minutes. Stirring was continued at ambient temperature for an additional 4 hours. The organic layer is separated, washed three times with water, once with 10% HCl, and once with saturated sodium bicarbonate. Evaporation of the ethyl acetate yielded 9.0 g of 1-methylaminocarbonyl-indane, an amide of Formula 13; (mp 107°-109° C.; ir 1635 cm-1).

Workup

  1. customas described in Preparation 4
  2. additionwas added over a period of 15 minutes
  3. customThe organic layer is separated
  4. washwashed three times with water
  5. customEvaporation of the ethyl acetate

Sources & evidence

ORD record
ord-5e56afdf8478495e8f5fd38169a5a788
Source dataset
uspto-grants-1990_09
Patent number
US04957914

Linked notes

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