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Methanol → (S)-3-Hydroxy-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide

HRID 1161208
Notes
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Reaction equation

HRID 1161208 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7]O[C:9]2=[O:14])([O-:3])=[O:2].CO.Cl.[NH2:18][C@@H:19]([CH2:23][OH:24])[C:20]([NH2:22])=[O:21].C(N(CC)CC)C>>[OH:24][CH2:23][C@H:19]([N:18]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[CH:13][C:4]=2[N+:1]([O-:3])=[O:2])[C:9]1=[O:14])[C:20]([NH2:22])=[O:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 100127605-nitro-1H-isochromen-1-oneHCID 16212403L-Serinamide hydrochloride

Product 1

HCID 59515781(S)-3-Hydroxy-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)propanamide

Conditions

Temperature
52 °C

Procedure

A round bottom flask was charged with 5-nitro-isochromen-1-one (2 g, 0.01 mol), methanol (40 mL, 1 mol), (S)-2-amino-3-hydroxypropanamide hydrochloride (2.2 g, 0.016 mol) and triethylamine (2.55 mL, 0.0183 mol) and stirred at 52° C. overnight. The product precipitated out and was filtered and dried to yield the pure product as a yellow solid. MS m/z=278.3 (M+H).

Workup

  1. customThe product precipitated out
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-777039749a5f45759a58efd3b375a755
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07816371B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes