Glycine → 2-(4-nitro-1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetic acid
Reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([O:9][C:10](=[O:11])[C:5]=12)=O)([O-:3])=[O:2].[NH2:15][CH2:16][C:17]([OH:19])=[O:18]>>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([N:15]([CH2:16][C:17]([OH:19])=[O:18])[C:10](=[O:11])[C:5]=12)=[O:9])([O-:3])=[O:2]Participants
Procedure
3-nitrophthalic anhydride (0.5 g, 0.0026 mol) and glycine (0.19 g, 0.0026 mol) were refluxed as above overnight. The clear solution was concentrated under vacuum with a rotary evaporator and the crude material triturated with hot 1,4-dioxane. Undissolved material was filtered through a Buchner funnel and washed twice with 1 ml hot 1,4-dioxane. The filtrate was diluted with water. A white solid appeared which was filtered through a Buchner and washed three times with 3–5 ml water. The product was dried in air for a short time and then in vacuo for 48–72 hours to afford 0.52 g (81%) 120 as off white crystals: mp=200–202° C.; Rf 0.73 (A): Rf 0.77 (C): Rf 0.23 (D): IR (cm−1): 2800–3200 (OH), 3096 (C═CH), 2652 (C—H), 1779 (C═O), 1724 (C═O), 1690 (C═O), 1648 (C═C), 1544 (N═O), 1470 (C═C), 1448 (C═C), 1412 (C—O), 1368 (N═O), 1260 (C—O), 722 (C═CH); MS m/z (rel intensity) 250 (15), 249 (100), 205 (89).
Workup
- concentrationThe clear solution was concentrated under vacuum with a rotary evaporator
- customthe crude material triturated with hot 1,4-dioxane
- filtrationwas filtered through a Buchner funnel
- washwashed twice with 1 ml hot 1,4-dioxane
- additionThe filtrate was diluted with water
- filtrationwas filtered through a Buchner
- washwashed three times with 3–5 ml water
- customThe product was dried in air for a short time
Sources & evidence
- ORD record
- ord-152f783af3ae493f8b0108eea659ec14
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07148352B2
Reaction notes
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