Ammonia → HCID 21914120, compound

HRID 887918Notes

Reaction equation

HRID 887918 reaction equation
[NH3:1].[F:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]([O:14]C)=O)[CH2:6]2>CO>[F:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]([NH2:1])=[O:14])[CH2:6]2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21914152HCID 21914152, compound

Product 1

HCID 21914120HCID 21914120, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 2M NH3 in methanol (0.6 mol), cooled in an ice bath under Ar, was added intermediate (16) (0.0574 mol) dissolved in methanol (150 ml). The mixture was allowed to warm to room temperature and stir under argon for 6 hours. The reaction was concentrated to 150 ml and filtered. The solid was rinsed with a small amount of cold methanol and allowed to dry, yielding 2.33 g of 5-fluoro-2,3-dihydro-1H-indole-2-carboxamide (intermediate 17, mp. 197-199° C.).

Workup

  1. concentrationThe reaction was concentrated to 150 ml
  2. filtrationfiltered
  3. washThe solid was rinsed with a small amount of cold methanol
  4. customto dry

Sources & evidence

ORD record
ord-9a766894afff4e4fb5a31cffc4cbfa28
Source dataset
uspto-grants-2012_08
Patent number
US08247432B2

Reaction notes

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