7-Iodonaphthalene-2-sulfonamide → 7-Hydroxynaphthalene-2-sulfonamide

HRID 528815Notes

Reaction equation

I[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.[O-:16]C1C=C2C(C=CC(S([O-])(=O)=O)=C2)=CC=1.[Na+].[Na+]>>[OH:16][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 710607367-Iodonaphthalene-2-sulfonamide

HCID 86718866Sodium 7-oxidonaphthalene-2-sulfonate

Product 1

HCID 7518327-Hydroxynaphthalene-2-sulfonamideYield 5%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 11, sodium 7-oxidonaphthalene-2-sulfonate (Pfaltz and Bauer, 1.00 g, 3.73 mmol) was converted to the title compound (40 mg, 5%) after purification using preparative HPLC. 1H NMR (DMSO-d6) δ 8.17 (s, 1H), 7.95 (d, J=8.6 Hz, 1H), 7.87 (d, J=8.8 Hz, 2H), 7.62 (dd, J=8.6, 1.8 Hz, 1H), 7.35 (s, 2H), 7.28 (d, J=2.2 Hz, 1H), 7.23 (dd, J=8.9, 2.3 Hz, 1H); MS(ESI−) m/z 236.3 (M−H)−.

Sources & evidence

ORD record: ord-e0d7393249744aedb439578bf78518ef
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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