9-Acetamido-6-carbethoxybenzo[a]phenoxazin-5-one → 9-Amino-6-carbethoxybenzo[a]phenoxazin-5-one

HRID 29029Notes

Reaction equation

HRID 29029 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]1[C:9](=[C:10]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:11](=[O:23])[C:12]3[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=31)[O:8]2)(=O)C>S(=O)(=O)(O)O.C(O)C.O>[NH2:4][C:5]1[CH:6]=[C:7]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]1[C:9](=[C:10]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:11](=[O:23])[C:12]3[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=31)[O:8]2

Participants

5

Reactant 1

HCID 685775359-Acetamido-6-carbethoxybenzo[a]phenoxazin-5-one

Product 1

HCID 685775199-Amino-6-carbethoxybenzo[a]phenoxazin-5-one

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

The 9-acetamido-6-carbethoxybenzo[a]phenoxazin-5-one obtained in point 3.2 was dissolved in a mixture of sulfuric acid (3 ml) and ethanol (3 ml). The mixture was heated to 80° C. while at the same time gradually adding water (1 ml). The purple color characteristic of the amine rapidly appeared. The hydrolysis was continued until the sample, diluted with water, and then extracted in ethyl acetate, no longer showed any 9-acetamido-6-carbethoxybenzo[a]phenoxazin-5-one by thin layer chromatography.

Workup

  1. extractionextracted in ethyl acetate

Sources & evidence

ORD record
ord-b3b0bc02a52a42b4aad122f36d54a3c7
Source dataset
uspto-grants-2008_09
Patent number
US07420054B2

Reaction notes

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