Chloral Hydrate → Acetamide, 2-(hydroxyimino)-N-phenyl-

HRID 2375554Notes

Reaction equation

[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].NC1C2C(=CC=CC=2)C=CC=1.ClC(Cl)(Cl)C(O)O.Cl.[NH2:31][OH:32].S([O-])([O-])(=O)=O.[Na+].[Na+]>>[CH:8]1[CH:7]=[CH:6][C:11]([NH:1][C:2](/[CH:4]=[N:31]/[OH:32])=[O:3])=[CH:10][CH:9]=1

Participants

Reactant 5

HCID 2707Chloral Hydrate

HCID 7054Isatin

HCID 86401-Naphthylamine

HCID 24436Sodium Sulfate

HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 6861488Acetamide, 2-(hydroxyimino)-N-phenyl-Yield 34%

Procedure

The procedure described above for the synthesis of intermediate 3 was followed, reacting 1-aminonaphthalene (10.0 g, 69.8 mmol) with chloral hydrate (13.9 g, 83.8 mmol) and hydroxylamine hydrochloride (17.5 g, 0.251 mol) in the presence of sodium sulfate (99 g, 0.70 mol). Isonitrosoacetanilide was obtained as a brownish-black solid (7.09 g, 47% yield).

Sources & evidence

ORD record: ord-7b66f0ee80814432a802f8e66fffa71a
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465798B2

Reaction notes

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