Hydrochloric Acid → HCID 657140, compound

HRID 1357385Notes

Reaction equation

HRID 1357385 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:35])[C:6]1[C:7](=[CH:12][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH:23][C:24](=[O:34])[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=2)=[CH:14][CH:15]=1)[C:8]([O:10]C)=[O:9].Cl>O1CCOCC1>[N+:31]([C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[C:24]([NH:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[O:16][C:13]1[CH:12]=[C:7]([C:8]([OH:10])=[O:9])[C:6](=[CH:15][CH:14]=1)[C:5]([OH:35])=[O:4])=[O:34])([O-:33])=[O:32]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9868369HCID 9868369, compound

Product 1

HCID 657140HCID 657140, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2N sodium hydroxide (12 ml) was added to a solution of 4-(2-(3-nitrobenzoylamino)-phenoxy)phthalic acid dimethylester (1.15 g, 2.83 mmol) in 1,4-dioxan (12 ml) at room temperature. The mixture was stirred for 2 hours, cooled to <10° C. and pH adjusted to 2-3 with 1N hydrochloric acid (approx. 24 ml). The resulting crystals were filtered off and washed with water. The crystals were dried to give beige crystals of 4-[2-(3-nitrobenzoylamino)-phenoxyl]phthalic acid (yield: 0.82 g. (76%)). 1H—NMR (CDCl3) in ppm: δ 10.3 (s, 1H), 8.38 (m, 1H), 8.18 (d, 1H), 7.6-7.8 (m, 3H), 7.3-7.4 (m, 2H), 7.18 (d.d., 1H), 7.1 (m, 1H), 7.07 (d.d., 1H). Mp: 199.7-201.0° C.

Workup

  1. temperaturecooled to <10° C.
  2. filtrationThe resulting crystals were filtered off
  3. washwashed with water
  4. customThe crystals were dried

Sources & evidence

ORD record
ord-590df919f76e4a2fa8b4eda0b4e75932
Source dataset
uspto-grants-2003_07
Patent number
US06590118B1

Reaction notes

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