Ammonia → HCID 136344259, compound

HRID 1669379Notes

Reaction equation

HRID 1669379 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[C:10](=[O:27])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([NH:21][CH2:22][C:23](OC)=[O:24])=[O:20])[CH:14]=1.[Cl-].[NH4+:29].N>>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[C:10](=[O:27])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([NH:21][CH2:22][C:23]([NH2:29])=[O:24])=[O:20])[CH:14]=1

Participants

4

Reactant 3

HCID 222Ammonia2×HCID 25517Ammonium ChlorideHCID 136344260HCID 136344260, compound

Product 1

HCID 136344259HCID 136344259, compoundYield 92%

Procedure

A mixture of 0.37 g of 4-hydroxy-3-[3-[3-[(methoxycarbonylmethyl)aminocarbonyl]phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone, 18 mg of ammonium chloride and 4 ml of aqueous concentrated ammonia was stirred at room temperature for 1 hour. Two ml of aqueous concentrated ammonia was added, and this was further stirred for 30 minutes, and concentrated under reduced pressure. The residue was washed with tetrahydrofuran, and the resulting crude crystals were recrystallized from dimethylformamide to obtain 0.11 g of 4-hydroxy-3-[3-[3-[(aminocarbonylmethyl)aminocarbonyl]phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone [Compound No. (91a)] as a yellow crystal.

Workup

  1. stirringthis was further stirred for 30 minutes
  2. concentrationconcentrated under reduced pressure
  3. washThe residue was washed with tetrahydrofuran
  4. customthe resulting crude crystals were recrystallized from dimethylformamide

Sources & evidence

ORD record
ord-c0820458b64e4441baf79ee0a74b76c2
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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