Ammonium Hydroxide → HCID 57926938, compound

HRID 1663179Notes

Reaction equation

HRID 1663179 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[O:6][CH2:5]2.[NH4+:12].[OH-]>CO>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([C:7]([NH2:12])=[O:11])=[C:4]([CH2:5][OH:6])[CH:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 6031445-Bromophthalide

Product 1

HCID 57926938HCID 57926938, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 5-bromoisobenzofuran-1(3H)-one III-1 (6.57 g, 30.1 mmol) in MeOH (140 mL) was added NH4OH (60 mL). The reaction vessel was sealed and stirred for 36 h. The reaction was The reaction was concentrated under vacuum to afford 4-bromo-2-(hydroxymethyl)benzamide (7.10 g, 99%) as a white solid; 1H-nmr (400 MHz, CDCl3) δ 7.80 (d, J=8.5 Hz, 1H), 7.70 (s, 1H), 7.68 (s, 2H), 7.61 (s, 1H), 7.59-7.50 (m, 2H), 6.34 (br s, 1H), 5.72 (br s, 1H), 4.64 (s, 2H); LC (254 nM) 1.12 min (>98%); MS (ESI) m/z=231.8.

Workup

  1. customThe reaction vessel was sealed
  2. concentrationwas concentrated under vacuum

Sources & evidence

ORD record
ord-b91ed0a8275047a8ada03262ff732525
Source dataset
uspto-grants-2011_10
Patent number
US08034806B2

Reaction notes

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