Hydrochloric Acid → 37494-82-9

HRID 2243185Notes

Reaction equation

HRID 2243185 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:12][CH3:13])C(=O)[O:8][C:9](=[O:10])[C:4]=2[CH:3]=1.Cl>[OH-].[K+]>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([NH:6][CH2:12][CH3:13])=[C:4]([CH:3]=1)[C:9]([OH:10])=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12223291HCID 12223291, compound

Product 1

HCID 1880316737494-82-9Yield 71%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
95 °C

Procedure

150 mg (0.67 mmol) of 6-chloro-1-ethyl-1H-benzo[d][1,3]oxazine-2,4-dione were suspended in 1.33 ml of 2N KOH and the mixture was heated to 95° C. for 2 h. After cooling to RT the pH was adjusted to 5-6 by careful addition of 1N HCl. The precipitate was then filtered off, washed with water and dried to give 93 mg (71%) of 5-chloro-2-ethylamino-benzoic acid as a yellow solid. 1HNMR (DMSO-d6, 300 MHz): δ 1.13 (t, J=7.2 Hz, 3H), 3.12 (q, J=7.2 Hz, 2H), 6.68 (d, J=9.1 Hz, 1H), 7.31 (dd, J=9.1 and 2.7 Hz, 1H), 7.64 (d, J=2.7 Hz, 1H).

Workup

  1. temperatureAfter cooling to RT the pH
  2. filtrationThe precipitate was then filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-a895d109a3fe41c6a1ce36636f3dea97
Source dataset
uspto-grants-2010_03
Patent number
US07674815B2

Reaction notes

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