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

HRID 1671630Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3CCCC[C:8]3=2)[C:3](=O)[C:2]1=[O:15].NC1C=CC=C2C=1CCC2.ClC(Cl)(Cl)C(O)O.Cl.[NH2:34][OH:35].S([O-])([O-])(=O)=O.[Na+].[Na+]>>[CH:6]1[CH:5]=[CH:4][C:9]([NH:1][C:2](/[CH:3]=[N:34]/[OH:35])=[O:15])=[CH:8][CH:7]=1

Participants

Reactant 5

HCID 2707Chloral Hydrate

HCID 24436Sodium Sulfate

HCID 1225694-Aminoindan

HCID 443297Hydroxyamine hydrochloride

HCID 137804146,7,8,9-Tetrahydro-1H-benzo[g]indole-2,3-dione

Product 1

HCID 6861488Acetamide, 2-(hydroxyimino)-N-phenyl-

Procedure

This was synthesized according to the procedure described above for intermediate 6. The isonitrosoacetanilide was prepared by reacting 4-aminoindane 8, (7.04 g, 52.9 mmol) with chloral hydrate (10.5 g, 63.4 mmol) and hydroxylamine hydrochloride (13.2 g, 0.190 mol) in the presence of sodium sulfate (75 g, 0.53 mol). Pure product 9 was obtained as a brown solid (7.18 g, 66% yield): 1H NMR (400 MHz, DMSO-D6) δ 2.00 (m, 2H) 2.80 (t, J=7.3 Hz, 2H) 2.88 (t, J=7.6 Hz, 2H) 7.05 (d, J=6.8 Hz, 1H) 7.12 (t, J=7.6 Hz, 1H) 7.45 (d, J=7.8 Hz, 1H) 7.71 (s, 1H) 9.49 (s, 1H) 12.19 (s, 1H).

Workup

customThis was synthesized

Sources & evidence

ORD record: ord-f159ed1fc1aa416aad3db6a9aaf46a5a
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994333B2

Reaction notes

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