2-Aminophenol → 2-Phenyl-3,4-dihydro-2H-1,4-benzoxazine

HRID 2052307Notes

Reaction equation

HRID 2052307 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.N[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1O.ClC1C=CC=CC=1CC(Cl)=O>>[C:12]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:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 58012-AminophenolHCID 182669Acetyl chloride, 2-(2-chlorophenyl)-HCID 5850963,4-Dihydro-2H-1,4-benzoxazine

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-b6c3eb7f61b2440d921b7836297b0dcf
Source dataset
uspto-grants-1980_01
Patent number
US04183936

Reaction notes

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