Ammonium Hydroxide → HCID 22452681, compound

HRID 2185880Notes

Reaction equation

HRID 2185880 reaction equation
S(Cl)(Cl)=O.[I:5][C:6]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[CH:9]=[C:8]([C:16](O)=[O:17])[C:7]=1[O:19][CH3:20].[NH4+:21].[OH-]>C1(C)C=CC=CC=1.CN(C=O)C>[I:5][C:6]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[CH:9]=[C:8]([C:16]([NH2:21])=[O:17])[C:7]=1[O:19][CH3:20]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 22452626HCID 22452626, compound

Product 1

HCID 22452681HCID 22452681, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (1.59 mL, 21.80 mmol) was added dropwise over 5 min to a stirred suspension of 4-iodo-3-methoxy-5,6,7,8-tetrahydro-2-naphthalenecarboxylic acid (2.9 g, 8.73 mmol) in toluene (10 mL) and DMF (0.25 mL) at room temperature. After heating at reflux for 3.5 h, the reaction was cooled to 0° C. and added to cooled (0° C.) 28% NH4OH (25 mL). The mixture was stirred at 0° C. for 10 min and at room temperature overnight. The mixture was filtered and the collected solid was thoroughly washed with H2O. The light brown solid (2.07 g, 72%) was dried under high vacuum at 50° C. 1H NMR (CDCl3) δ 7.79 (s, 1H), 7.61 (s, 1H), 5.90 (s, 1H), 3.84 (s, 3H), 2.76 (m, 4H), 1.79 (m, 4H). MS m/z 332 (M+H).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 3.5 h
  3. additionadded
  4. filtrationThe mixture was filtered
  5. washthe collected solid was thoroughly washed with H2O
  6. dry with materialThe light brown solid (2.07 g, 72%) was dried under high vacuum at 50° C

Sources & evidence

ORD record
ord-bbcc236cc2ba4ae69438a1a97fc57b23
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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