Hydrazine hydrate (1:1) → O-Benzylhydroxylamine

HRID 727153Notes

Reaction equation

HRID 727153 reaction equation
[C:1]1([CH2:7][O:8][N:9]2C(=O)C3=CC=CC=C3C2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN>C(O)C>[C:1]1([CH2:7][O:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 255292N-Benzyloxyphthalimide

Product 1

HCID 102313O-Benzylhydroxylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

When the bridging group n is =NOCH2 --, an appropriately substituted or unsubstituted phenylmethyl chloride, for example, 3-trifluoromethylphenylmethyl chloride, is reacted under basic conditions with N-hydroxyphthalimide in dimethyl sulfoxide, yielding the corresponding N-(phenylmethoxy)phthalimide. The so-prepared phthalimide is in turn reacted with hydrazine monohydrate in ethanol, affording an O-(phenylmethyl)hydroxylamine, for example, O-(3-trifluorophenylmethyl)hydroxylamine. The O-(phenylmethyl)hydroxylamine is then reacted with 2,4-di[(1,1-dimethylethyl)carbonylamino]-5,6,7,8-tetrahydro-6-quinazolinone, as described above, yielding the targeted 2,4-diamino-6-phenylmethoxyimino-5,6,7,8-tetrahydroquinazoline. Example 13 provides a detailed description of how this reaction is conducted.

Sources & evidence

ORD record
ord-d8dddc3874524675bd0ac198b8262700
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Reaction notes

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