Nitric Acid → HCID 131728508, compound

HRID 1173356Notes

Reaction equation

HRID 1173356 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:21])[C:8]2[O:14][C:13]3[C:15]([Cl:19])=[CH:16][CH:17]=[CH:18][C:12]=3[CH2:11][S:10][C:9]=2[CH:20]=1)=[O:4].[N+:22]([O-])([OH:24])=[O:23].S(=O)(=O)(O)[OH:27]>>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:21])[C:8]2[O:14][C:13]3[C:15]([Cl:19])=[CH:16][C:17]([N+:22]([O-:24])=[O:23])=[CH:18][C:12]=3[CH2:11][S:10](=[O:27])[C:9]=2[CH:20]=1)=[O:4]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 672474734-Chloro-6-methyl-11h-5-oxa-10-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Product 1

HCID 131728508HCID 131728508, compound

Procedure

Compound of Example 15b (4.1 g, 12.8 mmol) was added to solution of nitrating mixture (nitric acid 200 mL and sulfuric acid 20 mL) at 0° C. and stirred for 18 h. The reaction mixture was poured slowly with stirring into ice water (200 mL). The solid separated was filtered, washed with water and dried to obtain the title compound. Yield: 2.5 g, (52%); 1H NMR (CDCl3, 300 MHz): δ 2.65 (s, 3H, CH3), 3.93 (s, 3H, OCH3), 4.57 (s, 2H, CH2), 8.16 (d, 2H, Ar), 8.35 (d, 2H, Ar); MS: m/e (ES−) 380 (M−1).

Workup

  1. additionThe reaction mixture was poured slowly
  2. customThe solid separated
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-eccd75b8db494727a0d1f51c099a7f30
Source dataset
uspto-grants-2010_11
Patent number
US07834052B2

Reaction notes

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