Acetyl chloride, 2-(2-chlorophenyl)- → 2-Phenyl-3,4-dihydro-2H-1,4-benzoxazine

Reaction equation

[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][CH2:3][CH2:2]1.NO[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.ClC1C=CC=CC=1CC(Cl)=O>>[C:13]1([CH:2]2[CH2:3][NH:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[O:1]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Reactant 3

HCID 182669Acetyl chloride, 2-(2-chlorophenyl)-

HCID 5850963,4-Dihydro-2H-1,4-benzoxazine

HCID 2794249O-Phenylhydroxylamine

Product 1

HCID 137904912-Phenyl-3,4-dihydro-2H-1,4-benzoxazine

Procedure

By a procedure similar to that described for the synthesis of 3,4-dihydro-2H-1,4-benzoxazine (Example 142), O-aminophenol and 2-chlorophenylacetyl chloride produces 3,4-dihydro-2-phenyl-2H-1,4-benzoxazine, m.p. 113°-116° which, according to the reaction scheme of Example 110 is converted to the title compound, m.p. 311°-313° .

Sources & evidence

ORD record: ord-55bd5f9b727f4cdba6c52655b0178137
Source dataset: uspto-grants-1978_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04115577

Reaction notes

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