Ammonia → 2,3-dihydro-5-methoxy-1H-indole-2-carboxamide

HRID 887922Notes

Reaction equation

HRID 887922 reaction equation
C[O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH3:15])[CH:11]=2)[NH:6]1)=O.[NH3:16]>CO>[CH3:15][O:14][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[NH:6][CH:5]([C:3]([NH2:16])=[O:2])[CH2:13]2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 54121458(RS)-5-methoxy-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester

Product 1

HCID 219140882,3-dihydro-5-methoxy-1H-indole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,3-dihydro-5-methoxy-1H-indole-2-carboxylic acid methyl ester (0.084 mole) and 2M NH3 in methanol (500 ml) were combined and stirred at room temperature under argon over the weekend. The solution was concentrated to 100 ml, cooled in an ice bath, and filtered. The solid was rinsed with a small amount of cold methanol and dried. The residue was triturated in methanol/ACN and filtered, yielding 4.56 g of 2,3-dihydro-5-methoxy-1H-indole-2-carboxamide (intermediate 21, mp. 228-229° C.).

Workup

  1. concentrationThe solution was concentrated to 100 ml
  2. temperaturecooled in an ice bath
  3. filtrationfiltered
  4. washThe solid was rinsed with a small amount of cold methanol
  5. customdried
  6. customThe residue was triturated in methanol/ACN
  7. filtrationfiltered

Sources & evidence

ORD record
ord-208e38c56ce24e38a5c8c00a03161952
Source dataset
uspto-grants-2012_08
Patent number
US08247432B2

Reaction notes

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