Dimethylformamide → HCID 18929244, compound

HRID 1599829Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([NH2:12])=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].CN(C=O)C.[Br:18][CH2:19][C:20](Br)=[O:21]>O1CCOCC1>[CH3:1][O:2][C:3]1[C:4]([NH:12][C:20](=[O:21])[CH2:19][Br:18])=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7]

Participants

Conditions

Temperature: -5 °C

Procedure

A solution of 3-methoxy-2-aminobenzoic acid (5.0 g, 30 mmol) in a mixture of anhydrous DMF (30 mL) and anhydrous dioxane (30 mL) in a 250 mL-3-necked round-bottomed flask equipped with a constant addition funnel (60 mL) was cooled with an ice-bath to -5° C. Bromoacetyl bromide (6.66 g, 2.90 mL, 30 mmol) was added dropwise, keeping the internal temperature between -5° to 0° C. over a 1/2 h period. After the addition of bromoacetyl bromide was completed, the solution was warmed to room temperature and then stirred overnight. To the solution was slowly added 150 mL of ice-water, causing a pale white solid to precipitate. The precipitate was filtered, washed with water, and then dried in a vacuum oven overnight to afford 6.26 g (72%) of the title compound as a pale-white solid, mp 178°--180° C. (decomp): 1H NMR (DMSO-d6) δ12.80 (bs, 1H), 9.80 (s, 1H), 7.30-7.25 (m, 3H), 4.05 (s, 2H), 3.81 (s, 3H); 13C NMR (DMSO-d6) δ167.37, 164.54, 153.67, 129.76, 126.56, 124.39, 121.18, 114.66, 56.03, 29.63; MS (EI, m/z) 287 (M+).

Workup

customequipped with a constant addition funnel (60 mL)
custombetween -5° to 0° C.
customover a 1/2 h
temperaturethe solution was warmed to room temperature
customto precipitate
filtrationThe precipitate was filtered
washwashed with water
customdried in a vacuum oven overnight

Sources & evidence

ORD record: ord-fabbf4a334b841d1ba7615e90bbbfc47
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05741926

Reaction notes

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