Hydrochloric Acid → Methyl 10H-phenoxazine-4-carboxylate

HRID 1381658Notes

Reaction equation

HRID 1381658 reaction equation
C1(C([N:9]2[C:22]3[CH:21]=[CH:20][CH:19]=[C:18]([C:23]([O:25][CH3:26])=[O:24])[C:17]=3[O:16][C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=3)C)C=CC=CC=1.Cl.CCCCCC.C(OCC)(=O)C>C(O)(=O)C.[Zn]>[CH:21]1[C:22]2[NH:9][C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:16][C:17]=2[C:18]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14340230HCID 14340230, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 14031270Methyl 10H-phenoxazine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To 1.25 g of methyl N-(α-phenylethyl)phenoxazine-4-carboxylate in 25 ml of glacial acetic acid was added 500 g of zinc dust with stirring. To this stirred mixture, concentrated hydrochloric acid (2 ml) was added dropwise over a 5 minute period. At this time examination of the reaction mixture by TLC [silica gel, hexane:ethyl acetate (1:9)] showed that the starting material was consumed. The mixture was poured onto water, extracted with ethyl acetate, the extracted material was dried over sodium sulfate and the solvent removed under reduced pressure. Column chromatographic purification of the residue on silica gel (150 g) gave using the solvent system described above as the eluant gave a yellow solid, methyl phenoxazine-4-carboxylate, having mp 113°-114° C. after recrystallization from ethyl ether.

Workup

  1. customwas consumed
  2. additionThe mixture was poured onto water
  3. extractionextracted with ethyl acetate
  4. dry with materialthe extracted material was dried over sodium sulfate
  5. customthe solvent removed under reduced pressure
  6. customColumn chromatographic purification of the residue on silica gel (150 g)
  7. customgave

Sources & evidence

ORD record
ord-275ac1662f8a44ada8b6b967c4ac4851
Source dataset
uspto-grants-1989_02
Patent number
US04803269

Reaction notes

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