Aminoacetaldehyde dimethyl acetal → HCID 178498786, compound

HRID 595122Notes

Reaction equation

HRID 595122 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]2[N:6]=[C:7](SC)[CH2:8][O:9][C:4]=2[C:3]=1[C:14]([O:16][CH3:17])=[O:15].[CH3:18][O:19][CH:20]([O:23][CH3:24])[CH2:21][NH2:22]>C(O)C>[NH2:1][C:2]1[CH:13]=[CH:12][C:5]2[N:6]=[C:7]([NH:22][CH2:21][CH:20]([O:23][CH3:24])[O:19][CH3:18])[CH2:8][O:9][C:4]=2[C:3]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 86712826methyl 7-amino-3-methylsulfanyl-2H-benzo[1,4]oxazine-8-carboxylate2×

Product 1

HCID 178498786HCID 178498786, compoundYield 115.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 7-amino-3-methylsulfanyl-2H-benzo[1,4]oxazine-8-carboxylate (Intermediate 28, 0.645 g) and aminoacetaldehyde dimethylacetal (0.403 g) in ethanol (15 mL) was heated to reflux for 4 days. After cooling, the mixture was concentrated in vacuo to give methyl 7-amino-3-(2,2-dimethoxyethylamino)-2H-benzo[1,4]oxazine-8-carboxylate (0.910 g) as a brown oil.

Workup

  1. temperatureto reflux for 4 days
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-a6369f03db6b430e8fbf6954f7f4e7f0
Source dataset
uspto-grants-2016_01
Patent number
US09242997B2

Reaction notes

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