Ammonia → HCID 14451767, compound

HRID 451634Notes

Reaction equation

HRID 451634 reaction equation
S(O)(O)(=O)=O.[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:18][CH3:19])[C:14](OC)=[O:15])=[CH:9][CH:8]=1.[Na+].[Cl-].[NH3:22]>>[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:18][CH3:19])[C:14]([NH2:22])=[O:15])=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 5234Sodium Chloride2×HCID 86656427HCID 86656427, compound

Product 1

HCID 14451767HCID 14451767, compoundYield 90%

Conditions

Temperature
17.5 °C

Procedure

The methyl 4-aminophenylbutyrate hydrogensulfate, FW=291.11, 10.0 grams, 34.35 mmol, 1 eq) was dissolved in 20 ml of solution of 20% w/w aqueous NaCl (16 ml H2O and 4 grams of NaCl). To this solution aqueous ammonia (10 eq, 350 mmol, 14.8 molar solution, 24 ml) containing dissolved NaCl (4 grams) was added maintaining temperature 15-20° C. The mixture was stirred for 16 hours at RT. After that the mixture was cooled to 0-5° C. and held at this temperature for at least one hour. The resultant crystalline product was isolated by filtration. Washed with cold water (2 times for 10 ml) and dried under vacuum at 50° C. giving 5.5 g (90% yield) of 4-aminophenylbutyramide. C10H14N2O (MW 178.11); 1H NMR (500 MHz, DMSO-d6) δ: 7.23 ppm (br. s, 1H); 6.83 ppm (d, 2H, J=8.30 Hz); 6.68 ppm (br. s, 1H); 6.49 ppm (d, 2H, J=8.35 Hz); 4.80 ppm (br. s, 2H); 2.38 ppm (t, 2H, J=7.60 Hz); 2.03 ppm (t, 2H, J=7.53 Hz); 1.69 ppm (pentet, 2H, J=7.57 Hz).

Workup

  1. additionwas added
  2. temperatureAfter that the mixture was cooled to 0-5° C.
  3. waitheld at this temperature for at least one hour
  4. customThe resultant crystalline product was isolated by filtration
  5. washWashed with cold water (2 times for 10 ml)
  6. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-e0572dbd6ad94a23b6875204595b592b
Source dataset
uspto-grants-2013_07
Patent number
US08487130B2

Reaction notes

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